Alkyl sulfones

ABSTRACT

This invention relates to alkyl sulfones which are useful as herbicides and plant growth regulants.

RELATED APPLICATIONS

This application is a continuation-in-part of my copending application U.S. Ser. No. 227,886, filed Jan. 28, 1981, now abandoned, which is a continuation-in-part of my copending application U.S. Ser. No. 134,287, filed Mar. 26, 1980, now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to novel alkyl sulfones. The compounds of this invention and their agriculturally suitable salts, are useful as agricultural chemicals, e.g. plant growth regulants and herbicides.

Netherlands Pat. No. 121,788, published Sept. 15, 1966, discloses the preparation of compounds of the following Formula and their use as general or selective herbicides: ##STR1## wherein R₁ and R₂ may independently be alkyl of 1-4 carbon atoms; and

R₃ and R₄ may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms.

U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR2## wherein R₁ is hydrogen or lower saturated aliphatic acyl and

R₂ is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl.

The disclosed compounds are said to provide control of crabgrass, cress, endive, clover and Poa annua.

French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides as being useful as antidiabetic agents: ##STR3## wherein R=H, halogen, CF₃ or alkyl.

Logemann et al., Chem. Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR4## wherein R is butyl, phenyl or ##STR5## and R₁ is hydrogen or methyl.

When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.

Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR6##

U.S. Pat. No. 4,127,405 teaches compounds which are useful for controlling weeds in wheat having the formula ##STR7## wherein R is ##STR8## R₁ is ##STR9## R₃ and R₆ are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH₃ S(O)_(n) -- or CH₃ CH₂ S(O)_(n) --;

R₄ is hydrogen, fluorine, chlorine, bromine or methyl;

R₅ is hydrogen, fluorine, chlorine, bromine, methyl or methoxy;

R₇ is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atom;

R₈ is hydrogen, methyl, chlorine or bromine;

R₉ and R₁₀ are independently hydrogen, methyl, chlorine or bromine;

W and Q are independently oxygen or sulfur;

n is 0, 1 or 2;

X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH₃ S-- or CH₃ OCH₂ --; and

Z is methyl or methoxy;

or their agriculturally suitable salts; provided that:

(a) when R₅ is other than hydrogen, at least one of R₃, R₄, R₆ and R₇ is other than hydrogen and at least two of R₃, R₄, R₆ and R₇ must be hydrogen;

(b) when R₅ is hydrogen and all of R₃, R₄, R₆ and R₇ are other than hydrogen, then all of R₃, R₄, R₆ and R₇ must be either chlorine or methyl; and

(c) when R₃ and R₇ are both hydrogen, at least one of R₄, R₅ or R₆ must be hydrogen.

The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency. A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need still exists however, for more effective herbicides.

SUMMARY OF THE INVENTION

This invention pertains to novel compounds of Formula I, agriculturally suitable compositions containing them and their method-of-use as general or selective pre-emergent or post-emergent herbicides or plant growth regulants ##STR10## where R₁ is R₃ S(O)_(n) ;

R₂ is H, F, Cl, Br, CH₃, OCH₃, CF₃, NO₂, CN or NH₂ ;

R₃ is C₃ -C₄ alkyl, C₃ -C₄ alkenyl or cyclopropylmethyl;

n is 0, 1 or 2;

W is O or S;

Z is CH or N;

X is CH₃, C₂ H₅, CH₃ O, C₂ H₅ O or CH₂ OCH₃ ; and

Y is CH₃ or CH₃ O;

and their agriculturally suitable salts; provided that

(1) when R₂ is CN, then R₂ is not meta to R₁ ; and

(2) when W is S, then n is 0 or 2.

Preferred for reasons of their higher herbicidal activity, greater plant growth regulant activity or more favorable ease of synthesis are:

(1) Compounds of Formula I where W is 0.

(2) Compounds of Preferred 1 and where n is 2.

(3) Compounds of Preferred 2 where R₂ is H, Cl, CH₃, OCH₃ or CF₃.

(4) Compounds of Preferred 3 where X is CH₃ or OCH₃.

(5) Compounds of Preferred 4 where R₂ is H.

(6) Compounds of Preferred 5 where R₃ is C₃ alkyl.

Specifically Preferred for reasons of their highest herbicidal activity, treatest plant growth regulant activity or most favorable ease of synthesis are:

N-[(4,6-dimethylpyrimidin2-yl)aminocarbonyl]-2-[(1-methylethyl)sulfonyl]benzenesulfonamide;

N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-[(1-methylethyl)sulfonyl]benzensulfonamide;

N-[(4,6-dimethoxypyrimidin2-yl)aminocarbonyl]-2-[(1-methylethyl)sulfonyl]benzenesulfonamide;

N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-[(1-methylethyl)sulfonyl]benzenesulfonamide;

N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-[(1-methylethyl)sulfonyl]benzenesulfonamide;

N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-[(1-methylethyl)sulfonyl]benzenesulfonamide;

N-[(4,6-dimethylpyrimidin2-yl)aminocarbonyl]-2-(propylsulfonyl)benzenesulfonamide;

N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(propylsulfonyl)benzenesulfonamide;

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(propylsulfonyl)benzenesulfonamide;

N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(propylsulfonyl)benzenesulfonamide;

N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(propylsulfonyl)benzenesulfonamide; and

N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(propylsulfonyl)benzenesulfonamide.

This invention also relates to novel compounds of Formula II which are useful as intermediates for the synthesis of herbicidal sulfonylureas. ##STR11## wherein R₁ is S(O)_(n) R₃ ;

R₃ is C₃ -C₄ alkyl, C₃ -C₄ alkenyl orcyclopropylmethyl;

R₂ is H, F, Cl, Br, CH₃, OCH₃ CF₃, NO₂ or CN;

n is 0 or 2;

Q is NH₂ or NCW'; and

W' is O or S;

provided that when R₂ is CN, then R₂ may only be bonded to the 3 or 5 position of the benzene ring.

Preferred for their utility as intermediates for the preparation of herbicidal compounds with high activity and/or favorable ease of synthesis are:

(1) Compounds of Formula II where Q is NCW'.

(2) Compounds of Preferred 1 where W' is O.

(3) Compounds of Preferred 2 where n is 2.

(4) Compounds of Preferred 3 where R₃ is C₃ -C₄ alkyl.

(5) Compounds of Preferred 4 where R₂ is H, Cl, CH₃, OCH₃ or CF₃.

(6) Compounds of Preferred 5 where R₂ is H.

(7) Compounds of Preferred 6 where R₃ is C₃ alkyl.

(8) Compounds of Formula II where Q is NH₂.

(9) Compounds of Preferred 8 where n is 2.

(10) Compounds of Preferred 9 where R₃ is C₃ -C₄ alkyl.

(11) Compounds of Preferred 10 where R₂ is H, Cl, CH₃, OCH₃ or CF₃.

(12) Compounds of Preferred 11 where R₂ is H.

(13) Compounds of Preferred 12 where R₃ is C₃ alkyl.

Specifically Preferred for their utility as intermediates for the preparation of herbicidal compounds with higher activity and/or more favorable ease of synthesis are:

2-(propylsulfonyl)benzenesulfonylisocyanate;

2-(propylthio)benzenesulfonylisocyanate;

2-(1-methylethylsulfonyl)benzenesulfonylisocyanate;

2-(1-methylethylthio)benzenesulfonylisocyanate;

2-(propylsulfonyl)benzenesulfonamide;

2-(propylthio)benzenesulfonamide;

2-(1-methylethylsulfonyl)benzenesulfonamide;

2-(1-methylethylthio)benzenesulfonamide;

2-(propylsulfonyl)benzenesulfonylisothiocyanate;

2-(propylthio)benzenesulfonylisothiocyanate;

2-(1-methylethylsulfonyl)benzenesulfonylisothiocyanate; and

2-(1-methylethylthio)benzenesulfonylisothiocyanate.

SYNTHESIS

As shown in Equation 1, the compounds of Formula I can be prepared by reacting an appropriate 2-aminopyrimidine or 2-amino-1,3,5-triazine of Formula III with an appropriately substituted sulfonyl isocyanate or isothiocyanate of Formula IIa; R₁ is R₃ SO₂ or R₃ S; R₂, R₃, X, Y, Z and W are as previously defined. ##STR12##

The reaction is best carried out in an inert aprotic organic solvent such as methylene chloride, tetrahydrofuran or acetonitrile, at ambient pressure and temperature. The mode of addition is not critical; however, it is often convenient to add the sulfonyl isocyanate or isothiocyanate to a stirred suspension of amine III. Since such isocyanates and isothiocyanates are usually liquid, their addition can be easily controlled.

The reaction is generally exothermic. In some cases, the desired product is insoluble in the warm reaction medium and crystallizes from it in pure form. Products soluble in the reaction medium are isolated by evaporation of the solvent, trituration of the solid residue with solvents such as 1-chlorobutane or ethyl ether and filtration.

The intermediate sulfonyl isocyanate of Formula IIa can be prepared by reacting corresponding sulfonamides with phosgene in the presence of n-butyl isocyanate at reflux in a solvent such as xylene, according to the procedure of H. Ulrich and A. A. Y. Sayigh, Newer Methods of Preparative Organic Chemistry, Vol. VI, p. 223-241, Academic Press, New York and London, W. Foerst Ed. In cases where formation of the desired sulfonyl isocyanate is difficult by the above procedure, the sulfonylurea formed by the reaction of butyl isocyanate with the appropriate sulfonamide is treated with phosgene according to the above reference.

Some of the sulfonyl isocyanates used in this invention as intermediates are novel. These intermediates are prepared from the parent sulfonamides of Formula IIb as shown in Equation 2 by the reaction of the n-butylsulfonylurea with phosgene as described above. In Equation 2, R₁ is R₃ SO₂ or R₃ S and R₂ and R₃ are as previously defined. ##STR13##

A mixture of the appropriate sulfonylurea, IV and a catalytic amount of 1,4-diaza[2.2.2]bicyclooctane (DABCO) in xylene, chlorobenzene or other inert solvent of sufficiently high boiling point (e.g. 135° C.) is heated to approximately 135° C. Phosgene is added to the mixture until an excess of phosgene is present as indicated by a drop in the boiling point. The mixture is heated further to drive off the excess phosgene, cooled and filtered to remove a small amount of insoluble by-products. The solvent and alkylisocyanate are removed in vacuo leaving a residue which is the crude sulfonylisocyanate IIa.

The sulfonylisocyanates of Formula IIa may also be prepared by reacting the appropriate sulfonamides of Formula IIb with thionyl chloride and then phosgene as taught in EPO Publication No. 35893.

Certain compounds of Formula I are best prepared by heating a mixture of the arylsulfonylphenylcarbamate of Formula IIc and an appropriate 2-aminopyrimidine or 2-amino-1,3,5-triazine of Formula III in a solvent of sufficiently high boiling point, for example dioxane, as shown in Equation 3. The carbamates of Formula IIc are readily prepared from the corresponding sulfonamides of Formula IIb and diphenylcarbamate in the presence of base. ##STR14##

The compounds of Formula I can also be prepared from the sulfonamides of Formula IIb and the appropriate heterocyclic carbamate of Formula IIIa as shown in Equation 4. Contacting IIb with trimethylaluminum is followed by addition of IIIa. Heating the resulting mixture in dichloromethane will give I after acidic workup. The heterocyclic carbamates of Formula IIIa can be readily prepared from the corresponding amines III by standard literature procedures. ##STR15##

Sulfonylisothiocyanates can be prepared by treatment of sulfonamides with carbon disulfide and potassium hydroxide followed by reaction of the dipotassium salt with phosgene according to the teaching of K. Hartke, Arch. Pharm., 229, 174 (1966).

The sulfonamides of Formula IIb wherein n=1 can be prepared by a variety of procedures reported in the literature. As shown in Equation 5, the thioether of Formula VI may be prepared from the appropriate 2-aminothiophenol V and an alkyl halide as described in the literature, e.g., R. N. Prasad et al., Can. J. Chem., 44, 1247 (1966). The formation of the benzenesulfonyl chloride and the corresponding sulfonamide IId has been previously described (co-pending application U.S. Ser. No. 192,034, filed Sept. 29, 1980). The oxidation of IId to the corresponding 2-alkylsulfonylbenzenesulfonamides of Formula IIe may be carried out utilizing a variety of standard literature procedures, including m-chloroperbenzoic acid (C. R. Johnson, et al., Tetradedron 25, 5649 (1969)), or with aqueous hydrogen peroxide in acetic acid (F. G. Bordwell, et al., J. Amer. Chem. Soc., 77, 1141 (1955)). ##STR16##

Compounds of Formula IIb wherein n≠1 may also be prepared from 2-halonitrobenzenes of Formula VII as outlined in Equation 6. Halide displacement in VII by thiols (n=0) or sulfinates (n=2) is widely reported in the literature (for general reviews see, "Organic Chemistry of Sulfur", S. Oae, ed., Plenum Press, New York, 1977, pp. 232-233; Reid, "Organic Chemistry of Bivalent Sulfur," Chemical Publishing Co., New York, Vol. 2, pp. 16-21, 24-29; Vol. 3, pp. 11-14; Peach, in Patai, "The Chemistry of the Thiol Group," pt. 2, pp. 735-744, John Wiley and Sons, Inc., New York, 1974). ##STR17##

Compounds of Formula IX (n=0 or 2) may also be prepared as shown in Equation 7 (in addition to references cited above, see, Zh Obshch. Khim, 35 (8) 1361 (1965) and J. Chem. Soc., 763 (1946)). Reduction of IX to the amine X can be carried out by a variety of standard literature procedures, including catalytic hydrogenation (Rylander, "Catalytic Hydrogenation over Platinum Metals," pp. 168-202, Academic Press, Inc., New York, 1967) and reduction with iron (D. Cowsley et al., Synthesis 118 (1977)) or stannous chloride (Org. Synth., Coll. Vol. 2, 130 (1943); ibid, 3, 240, 453 (1955)) in acidic medium. Conversion of X to IIb has been discussed previously (Equation 5). ##STR18##

In some cases it is best to oxidize the thioethers of Formula IXa to the corresponding sulfones IXb prior to reduction and subsequent diazotization, as shown in Equation 8. ##STR19##

Ortho-lithiation of appropriately substituted benzene derivatives also provides a route to sulfonamides of Formula IIb. As shown in Equation 9, the t-butylbenzenesulfonamides of Formula XI may be ortho-lithiated [for general review, see H. W. Gschwend et al., Organic Reactions, 26, 1 (1979)] and then trapped with sulfur, followed by alkyl halide, or disulfide to give sulfonamides of Formula IId [S. Gronowitz et al., Acta. Chem. Scand., 21, 812 (1967) and Chem. Ber., 99, 3215 (1966)]. Treatment of XII with sulfur dioxide, followed by alkyl halide will give sulfonamides of Formula IIe [JACS, 74, 5177 (1952)]. ##STR20##

The lithium sulfonates of Formula XIII can also be ortho-lithiated to give compounds of Formula XIV as shown in Equation 10. Treatment of XIV with sulfur electrophiles as in Equation 9 will give the sulfonates of Formula XV (for example, see J. C. Martin et al., JOC, 45, 3728 (1980)]. Conversion of XV to the sulfonamides of Formula IIb can be accomplished using thionyl chloride and a catalytic amount of dimethylformamide and then treating the sulfonyl chloride with ammonia. ##STR21##

Sulfonamides of Formula IId can also be prepared by reaction of the chlorosulfonamides of Formula IIf and the appropriate mercaptan of Formula XVI in a high boiling solvent, for example, dimethylformamide, as shown in Equation 11. The preparation of the sulfonamides IIf is described in U.S. Pat. No. 4,169,719 and U.S. Pat. No. 4,127,405, which are herein incorporated by reference. ##STR22##

Compounds of Formula I may also be prepared by the reaction of the substituted sulfonamides of Formula IIb with an appropriate heterocyclic isocyanate as previously described (co-pending applications U.S. Ser. No. 098,725 and U.S. Ser. No. 098,772).

Compounds of Formula Ib, where R₁ is equal to SOR₃ can be prepared from the appropriate compounds of Formula Ia where R₁ is equal to SR₃ ; R₂, X, Y and Z being as previously defined, by oxidation with m-chloroperbenzoic acid according to Equation 12. ##STR23##

The reaction can be carried out by mixing equivalent amounts of Ia with m-chloroperbenzoic acid in an inert solvent such as chloroform and stirring at 0° C. to reflux for 12-24 hours after which the insoluble m-chlorobenzoic acid produced is removed by filtration and the chloroform solution containing the desired sulfoxide is concentrated to yield the crude product. The product can be purified further by dissolving it in aqueous base of pH 10 and adjusting the pH to 4 to precipitate the desired compound while leaving the m-chlorobenzoic acid in solution as its sodium salt. Treatment of Ia with one equivalent of hydrogen peroxide in glacial acetic acid at 0° C. to room temperature will also give sulfoxide Ib.

The synthesis of heterocyclic amine derivatives has been reviewed in "The Chemistry of Heterocyclic Compounds," a series published by Interscience Publ., New York and London. 2-Aminopyrimidines are described by D. J. Brown in "The Pyrimidines", Vol. XVI of the above series. 2-Amino-1,3,5-triazines can be synthesized according to the methods described by E. M. Smolin and L. Rapaport in "s-Triazines and Derivatives," Vol. XIII of the same series.

Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by contacting compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonate or hydroxide). Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of one cation for another. Cationic exchange can be effected by direct contact of an aqueous solution of a salt of a compound of Formula I (e.g., alkali or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration.

Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble.

Acid addition salts, useful in this invention, can be obtained by reacting a compound of Formula I with a suitable acid, e.g., p-toluenesulfonic acid, trichloroacetic acid or the like.

The compounds of this invention and their preparation are further illustrated by the following examples wherein temperatures are given in degrees centigrade and parts are by weight unless otherwise designated.

EXAMPLE 1 2-(1-Methylethylthio)benzenamine

To a solution of 2-aminothiophenol (90%, 100 g, 0.72 mol) and sodium hydroxide (31.7 g, 0.792 mol) in 90% aqueous ethanol (500 ml) was added dropwise 2-bromopropane (89 g, 0.72 mol) at room temperature. When the addition was complete, the reaction mixture was refluxed for 3 hours, cooled to room temperature, and then concentrated in vacuo. The residue was diluted with water (300 ml) and extracted with ether (3×500 ml). The ether extracts were washed with water and brine, dried with MgSO₄ and concentrated in vacuo to yield the crude product. Distillation through a Vigreaux column gave 2-(1-methylethylthio)benzenamine: bp 94° (2.2-2.4 mm).

NMR (CDCl₃)δ: 1.25 (d, 6H, --CH₃), 3.15 (hept., 1H, --CH--); 4.25 (broad s, 2H, --NH₂); 6.40-7.40 (m, 4H, Ar--H).

EXAMPLE 2 2-(1-Methylethylthio)benzenesulfonamide

To a solution of 2-(1-methylethylthio)benzenamine (200 g, 1.20 mol) in a mixture of concentrated hydrochloric acid (420 ml) and glacial acetic acid (120 ml) was added a solution of sodium nitrile (91.2 g, 1.32 mol) in water (180 ml) at -5° to 0°. The solution was stirred at 0° for 1/2 hour and then poured, in several portions, into a mixture of cupric chloride dihydrate (24 g) and liquid sulfur dioxide (370 ml, 8.28 mol), in glacial acetic acid (1200 ml) at 0°. The resulting solution was stirred at 0° for one hour and then allowed to warm to room temperature. After several hours, ether (1000 ml) was added, and the reaction mixture was stirred overnight and then poured into ice-water. The resulting oil was extracted into dichloromethane. The organic extracts were washed with water and 5% aqueous sodium bicarbonate (until neutral), dried (MgSO₄) and concentrated in vacuo to give an oil. The crude sulfonyl chloride was dissolved in dry THF (2000 ml) and treated with anhydrous liquid ammonia (50 ml, 2.3 mol) at 0°. The solution was stirred at 0° for one hour, allowed to warm to room temperature, and stirred an additional 2.5 hours. The reaction mixture was concentrated in vacuo, and the residue was diluted with water (1000 ml) and extracted with dichloromethane. The extracts were washed with water, dried (MgSO₄) and concentrated to yield the crude product. The oil was dissolved in hot (60°) hexane/n-butyl chloride (5/2). Upon cooling, 2-(1-methylethylthio)benzenesulfonamide settled out as a dark oil.

NMR (CDCl₃)δ: 1.30 (d, --CH₃); 3.60 (hept. --CH--); 5.75 (broad s, --NH₂); 7.0-8.2 (m, Ar--H).

IR (Nujol): 3200-3300 doublet); 1300 and 1150 cm⁻¹.

EXAMPLE 3 2-[(1-Methylethyl)sulfonyl]benzenesulfonamide

To a solution of 2-[(1-methylethyl)thio]benzenesulfonamide (79 g, 0.34 mol) in glacial acetic acid (200 ml) was added dropwise 30% aqueous hydrogen peroxide (100 ml, 1.16 mol) at room temperature. When the addition was complete, the reaction mixture was heated to 80° for 2 hours and then allowed to cool to room temperature. Addition of ice-water resulted in the precipitation of 2-[(1-methylethyl)sulfonyl]benzenesulfonamide as a light-yellow solid, m.p. 150°-153°.

NMR (CDCl₃)δ: 1.25 (d, --CH₃); 4.20 (hept, --CH--); 6.90 (broad s, --NH₂); 7.60-8.40 (m, Ar--H).

IR (KBr) 3400-3300 (d), 1330, 1290, 1160 and 1130 cm⁻¹.

EXAMPLE 4 N-[Butylaminocarbonyl]-2-[(1-methylethyl)sulfonyl]benzenesulfonamide

A mixture of 2-[(1-methylethyl)sulfonyl]benzenesulfonamide (29 g, 0.11 mol), n-butylisocyanate (14.7 g, 0.15 mol) and anhydrous potassium carbonate (16.6 g, 0.120 mol) in methylethyl ketone (325 ml) was refluxed with stirring for 3 hours. The reaction mixture was cooled to 0° and then poured into ice-water. The aqueous solution was acidified to pH 1 with concentrated hydrochloric acid. The resulting precipitate was filtered, washed with water and recrystallized from ethanol to give N-[butylaminocarbonyl]-2-[(1-methylethyl)sulfonyl]benzenesulfonamide, m.p. 164.5°-165.5°.

NMR (DMSO)δ: 0.6-1.6 (m, 13H, --(CH₂)₂ --, --CH₃); 2.7-3.20 (m, 2H, --CH₂ --); 4.15 (hept, 1H, --CH--); 6.85 (t, 1H, --NH--); 7.8-8.5 (m, 4.6H, Ar--H, --NH--).

IR (KBr) 3300, 1660, 1430, 1310, 1170 and 1130 cm⁻¹.

EXAMPLE 5 2-[(1-Methylethyl)sulfonyl)benzenesulfonyl isocyanate

A solution of N-[butylaminocarbonyl]-2-[(1-methylethyl)sulfonyl]benzenesulfonamide (17.4 g, 0.048 mol) and 1.4-diaza[2,2,2]bicyclooctane (0.1 g) in mixed xylenes (90 ml) was heated to 135°-140°. Liquid phosgene (3.6 ml, 0.050 mol) was added at a rate to maintain an internal temperature between 125°-135°. When the addition was complete, the solution was refluxed for 2 hours, cooled to room temperature and then filtered under a nitrogen atmosphere. Removal of solvent in vacuo gave 2-[(1-methylethyl)sulfonyl]benzenesulfonyl isocyanate, which was used immediately without further purification.

EXAMPLE 6 N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2-[(1-methylethyl)sulfonyl]benzenesulfonamide

A solution of 2-[(1-methylethyl)sulfonyl]benzenesulfonyl isocyanate (2.3 g, 0.008 mol) in dichloromethane (12 ml) was added to 2-amino-4,6-dimethylpyrimidine (0.74 g, 0.006 mol) and DABCO (catalytic amount) and the suspension was stirred overnight at room temperature. The solvent was removed in vacuo and acetonitrile was added to the residue. The precipitated solid was filtered and dried to give N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-[(1-methylethyl)sulfonyl]benzenesulfonamide as a white powder, m.p. 188°-193° (dec.).

NMR (CDCl₃)δ: 1.30 (d, --C(CH₃)₂); 2.45 (s, het--CH₃); 6.75 (s, het--H).

IR (KBr) 1700, 1600, 1550, 1420, 1330, 1300 1160 and 1130 cm⁻¹.

EXAMPLE 7 2-(1-Propylthio)benzenesulfonamide

To a solution of potassium hydroxide (85%, 12 gm, 0.2 mole) and n-propylmercaptan (18.1 ml, 0.2 mole) in 100 ml dimethylformamide at 90° C. was added a solution of 2-chlorobenzenesulfonamide (19.1 gm, 0.1 mole) in 100 ml dimethylformamide. The reaction mixture was heated to reflux for five hours, cooled, and the solvent was removed in vacuo. The residue was diluted with water, made acidic with concentrated hydrochloric acid and extracted with ether. The ether extracts were washed with water and brine, dried over MgSO₄ and concentrated in vacuo to yield the crude product. Recrystallization from a suitable solvent such as toluene afforded 19 gm (82%) product: m.p. 58°-64°.

NMR (CDCl₃)δ: 1.0 (t, 3H, --CH₃); 1.8 (m, 2H, --CH₂ --); 3.1 (t, 2H, --SCH₂); 5.2 (s, 2H, --NH₂); and 7.2-8.0 (m, 4H, --ArH).

EXAMPLE 8 2-(1-Propylsulfonyl)benzenesulfonamide

To a solution of 2-(2-propylthio)benzenesulfonamide (19 gm, 0.082 mole) in glacial acetic acid (50 ml) was added dropwise 30% aqueous hydrogen peroxide (25 ml, 0.3 mole) at room temperature. When the addition was complete, the reaction mixture was heated to 80° C. for 2 hours and then allowed to cool to room temperature. Addition of ice-water resulted in the precipitation of 2-(1-propylsulfonyl)benzenesulfonamide as a light yellow solid, m.p. 122°-124°.

NMR (CDCl₃)δ: 1.0 (t, 3H, --CH₃); 1.7 (m, 2H, --CH₂); 3.4 (t, 2H, --CH₂); 5.2 (s, 2H, NH₂); and 7.5-8.2 (m, 4H, ArH).

EXAMPLE 9 N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2-(1-propylsulfonyl)benzenesulfonamide

A solution of 2-(1-propylsulfonyl)benzenesulfonamide (10 gm, 0.04 mole) in 80 ml thionyl chloride was heated to reflux for 6-16 hours. The reaction progress was monitored by NMR and shown to be complete by the disappearance of SO₂ NH₂ at 5.2δ. The thionyl chloride was removed in vacuo and to the residue was added 80 ml of a 10% (by weight) solution of phosgene in toluene. Three drops of pyridine were added and the reaction was heated to reflux for 3 hours, cooled, and filtered. The solvent was removed in vacuo to yield the crude sulfonyl isocyanate: IR 2230 cm⁻¹. The sulfonyl isocyanate was dissolved in 50 ml dry acetonitrile and added to a solution of 2-amino-4,6-dimethylpyrimidine (4.3 gm, 0.035 mole) in 50 ml dry acetonitrile. The solution was stirred overnight at room temperature and the precipitated solid was filtered and dried to give N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(1-propylsulfonyl)benzenesulfonamide as a white powder, m.p, 200°14 202°(dec).

Using procedures similar to those given in Examples 1-9 and Equations 1-12, the following compounds may be prepared.

                                      TABLE I                                      __________________________________________________________________________      ##STR24##                                                                     n  R.sub.2                                                                            R.sub.3    X     Y     W  m.p. (°C.)                             __________________________________________________________________________     2  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             CH.sub.3                                                                             O  200-202(D)                                    2  H    -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            CH.sub.3                                                                             O  183-185(D)                                    2  H    -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O  215-217                                       2  H   CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                             CH.sub.3                                                                             O  188-193(D)                                    2  H   CH(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                            CH.sub.3                                                                             O  189-192                                       2  H   CH(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                            O  237-239                                       2  H    -n-C.sub.4 H.sub.9                                                                       CH.sub.3                                                                             CH.sub.3                                                                             O  179-181.5(D)                                  2  H    -n-C.sub.4 H.sub.9                                                                       OCH.sub.3                                                                            CH.sub.3                                                                             O  152-155                                       2  H    -n-C.sub.4 H.sub.9                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O  177-183                                       2  H   CH.sub.2 CH(CH.sub.3).sub.2                                                               CH.sub.3                                                                             CH.sub.3                                                                             O  185-191                                       2  H   CH.sub.2 CH(CH.sub.3).sub.2                                                               OCH.sub.3                                                                            CH.sub.3                                                                             O  180-185                                       2  H   CH.sub.2 CH(CH.sub.3).sub.2                                                               OCH.sub.3                                                                            OCH.sub.3                                                                            O  215-218                                       2  H   CH(CH.sub.3)C.sub.2 H.sub.5                                                               CH.sub.3                                                                             CH.sub.3                                                                             O  174-178(D)                                    2  H   CH(CH.sub.3)C.sub.2 H.sub.5                                                               OCH.sub.3                                                                            CH.sub.3                                                                             O  198-203                                       2  H   CH(CH.sub.3)C.sub.2 H.sub.5                                                               OCH.sub.3                                                                            OCH.sub.3                                                                            O  203-213                                       2  H   C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                             CH.sub.3                                                                             O  190-195(D)                                    2  H   C(CH.sub.3).sub.3                                                                         OCH.sub.3                                                                            CH.sub.3                                                                             O  192-195                                       2  H   C(CH.sub.3).sub.3                                                                         OCH.sub.3                                                                            OCH.sub.3                                                                            O  217-218                                       0  H   CH.sub.2 CHCH.sub.2                                                                       CH.sub.3                                                                             CH.sub.3                                                                             S                                                0  5-F CH CHC.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                            S                                                0  3-Cl                                                                               CH.sub.2 CH.sub.2 CHCH.sub.2                                                              OC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                            S                                                0  6-Br                                                                               CHCHCH.sub.3                                                                              CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                                                             S                                                1  6-NO.sub.2                                                                          ##STR25## C.sub.2 H.sub.5                                                                      CH.sub.3                                                                             O                                                1  5-CN                                                                                ##STR26## OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                1  6-NH.sub.2                                                                          ##STR27## CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                            O                                                0  H    -n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                      CH.sub.3                                                                             O                                                0  H    -n-C.sub.3 H.sub.7                                                                       OC.sub.2 H.sub.5                                                                     CH.sub.3                                                                             O                                                0  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                                                             O                                                0  H    -n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                            O                                                0  H    -n-C.sub.3 H.sub.7                                                                       OC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                            O                                                0  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                            O                                                2  H    -n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                      CH.sub.3                                                                             O                                                2  H    -n-C.sub.3 H.sub.7                                                                       OC.sub.2 H.sub.5                                                                     CH.sub.3                                                                             O                                                2  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                                                             O                                                2  H    -n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                            O                                                2  H    -n-C.sub.3 H.sub.7                                                                       OC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                            O                                                2  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                            O                                                2  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             CH.sub.3                                                                             S                                                2  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            S                                                2  H    -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            S                                                0  H   CH(CH.sub.3).sub.2                                                                        C.sub.2 H.sub.5                                                                      CH.sub.3                                                                             O                                                0  H   CH(CH.sub.3).sub.2                                                                        OC.sub.2 H.sub.5                                                                     CH.sub.3                                                                             O                                                0  H   CH(CH.sub.3 ).sub.2                                                                       CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                                                             O                                                0  H   CH(CH.sub.3).sub.2                                                                        C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                            O                                                0  H   CH(CH.sub.3).sub.2                                                                        OC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                            O                                                0  H   CH(CH.sub.3).sub.2                                                                        CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                            O                                                2  H   CH(CH.sub.3).sub.2                                                                        C.sub.2 H.sub.5                                                                      CH.sub.3                                                                             O                                                2  H   CH(CH.sub.3).sub.2                                                                        OC.sub.2 H.sub.5                                                                     CH.sub.3                                                                             O                                                2  H   CH(CH.sub.3).sub.2                                                                        CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                                                             O                                                2  H   CH(CH.sub.3).sub.2                                                                        C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                            O                                                2  H   CH(CH.sub.3).sub.2                                                                        OC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                            O                                                2  H   CH(CH.sub.3).sub.2                                                                        CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                            O                                                2  H   CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                             CH.sub.3                                                                             S                                                2  H   CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                             OCH.sub.3                                                                            S                                                2  H   CH(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                            S                                                0  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             CH.sub.3                                                                             O  191-200(D)                                    0  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            O  160-165                                       0  H    -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O  165-170                                       1  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             CH.sub.3                                                                             O  110-116                                       1  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            O   80-96                                        1  H    -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O  175-178                                       0  H   CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                             CH.sub.3                                                                             O                                                0  H   CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                             OCH.sub.3                                                                            O                                                0  H   CH(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                1  H   CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                             CH.sub.3                                                                             O                                                1  H   CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                             OCH.sub.3                                                                            O                                                1  H   CH(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                0  H                                                                                   ##STR28## CH.sub.3                                                                             CH.sub.3                                                                             O                                                0  H                                                                                   ##STR29## CH.sub.3                                                                             OCH.sub.3                                                                            O                                                0  H                                                                                   ##STR30## OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  H                                                                                   ##STR31## CH.sub.3                                                                             CH.sub.3                                                                             O  198-199°                               2  H                                                                                   ##STR32## CH.sub.3                                                                             OCH.sub.3                                                                            O  196-198°                               2  H                                                                                   ##STR33## OCH.sub.3                                                                            OCH.sub.3                                                                            O  226-227°                               0  H   CH.sub.2 CHCH.sub.2                                                                       CH.sub.3                                                                             CH.sub.3                                                                             O  198-203°                               0  H   CH.sub.2 CHCH.sub.2                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            O  175-177°                               0  H   CH.sub.2 CHCH.sub.2                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O  181-186°                               2  H   CH.sub.2 CHCH.sub.2                                                                       CH.sub.3                                                                             CH.sub.3                                                                             O  173-180°                               2  H   CH.sub.2 CHCH.sub.2                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            O  185-190°                               2  H   CH.sub.2 CHCH.sub.2                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O  228- 232°                              2  H   CH(CH.sub.3)CHCH.sub.2                                                                    CH.sub.3                                                                             CH.sub.3                                                                             O                                                2  H   CH(CH.sub.3)CHCH.sub.2                                                                    CH.sub.3                                                                             OCH.sub.3                                                                            O                                                2  H   CH(CH.sub.3)CHCH.sub.2                                                                    OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  H   CH.sub.2 CH.sub.2 CHCH.sub.2                                                              CH.sub.3                                                                             CH.sub.3                                                                             O                                                2  H   CH.sub.2 CH.sub.2 CHCH.sub.2                                                              CH.sub.3                                                                             OCH.sub.3                                                                            O                                                2  H   CH.sub.2 CH.sub.2 CHCH.sub.2                                                              OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                0  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             CH.sub.3                                                                             S                                                0  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            S                                                0  H    -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            S                                                0  H   CH.sub.2 CHCH.sub.2                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            S                                                2  H   CHCHCH.sub.3                                                                              OCH.sub.3                                                                            CH.sub.3                                                                             O                                                2  H   CHCHCH.sub.2 CH.sub.3                                                                     OCH.sub.3                                                                            CH.sub.3                                                                             O                                                2  H   CH.sub.2 CH.sub.2 CHCH.sub.2                                                              OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  H   CH.sub.2 CHCHCH.sub.3                                                                     OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  3-F  -n-C.sub.3 H.sub. 7                                                                      CH.sub.3                                                                             OCH.sub.3                                                                            O                                                2  6-F  -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             CH.sub.3                                                                             O                                                2  3-NO.sub.2                                                                          -C.sub.3 H.sub.7                                                                         OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  5-Cl                                                                                -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            CH.sub.3                                                                             O                                                2  6-Cl                                                                                -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  3-Br                                                                                -n-C.sub.4 H.sub.9                                                                       OCH.sub.3                                                                            CH.sub.3                                                                             O                                                2  5-Br                                                                                -C.sub.4 H.sub.9                                                                         OCH.sub.3                                                                            CH.sub.3                                                                             O                                                2  3-CH.sub.3                                                                          -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             OCH.sub.2 CH.sub.3                                                                   O                                                2  5-NO.sub.2                                                                          -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            O                                                2  5-CH.sub.3                                                                          -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  6-CH.sub.3                                                                          -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  3-CF.sub.3                                                                          -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            CH.sub.3                                                                             O                                                2  6-NO.sub.2                                                                          -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            O                                                2  5-CF.sub.3                                                                           -n-C.sub.3 H.sub.7                                                                      CH.sub.3                                                                             OCH.sub.3                                                                            O                                                2  6-CF.sub.3                                                                          -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             CH.sub.3                                                                             O                                                2  3-CN                                                                                -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  5-CN                                                                                -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  H    -n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                            O                                                2  H    -n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                      CH.sub.3                                                                             O                                                2  H    -n-C.sub.3 H.sub.7                                                                       OC.sub.2 H.sub.5                                                                     CH.sub.3                                                                             O                                                2  H    -n-C.sub.3 H.sub.7                                                                       OC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                            O                                                2  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                                                             O                                                2  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                            O                                                1  H   CH.sub.2 CHCH.sub.2                                                                       CH.sub.3                                                                             CH.sub.3                                                                             O                                                1  H   CH.sub.2 CHCH.sub.2                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            O                                                1  H   CH.sub.2 CHCH.sub.2                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                __________________________________________________________________________

                                      TABLE II                                     __________________________________________________________________________      ##STR34##                                                                     n  R.sub.2                                                                            R.sub.3    X     Y     W  m.p. (°C.)                             __________________________________________________________________________     2  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             CH.sub.3                                                                             O  189-191° (D)                           2  H    -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            CH.sub.3                                                                             O  200-201°(D)                            2  H    -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O  184-187°                               2  H   CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                             CH.sub.3                                                                             O  115-119°                               2  H   CH(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                            CH.sub.3                                                                             O  108-126°                               2  H   CH(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                            O  108-130°                               2  H    -n-C.sub.4 H.sub.9                                                                       CH.sub.3                                                                             CH.sub.3                                                                             O  173-178°                               2  H    -n-C.sub.4 H.sub.9                                                                       OCH.sub.3                                                                            CH.sub.3                                                                             O  173-177°                               2  H    -n-C.sub.4 H.sub.9                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O  175-179°                               2  H   CH.sub.2 CH(CH.sub.3).sub.2                                                               CH.sub.3                                                                             CH.sub.3                                                                             O  180-183°                               2  H   CH.sub.2 CH(CH.sub.3).sub.2                                                               OCH.sub.3                                                                            CH.sub.3                                                                             O  175-178°                               2  H   CH.sub.2 CH(CH.sub.3).sub.2                                                               OCH.sub.3                                                                            OCH.sub.3                                                                            O  180-188°                               2  H   CH(CH.sub.3)C.sub.2 H.sub.5                                                               CH.sub.3                                                                             CH.sub.3                                                                             O  160-163°                               2  H   CH(CH.sub.3)C.sub.2 H.sub.5                                                               OCH.sub.3                                                                            CH.sub.3                                                                             O  170-173.5°                             2  H   CH(CH.sub.3)C.sub.2 H.sub.5                                                               OCH.sub.3                                                                            OCH.sub.3                                                                            O  173-181°                               2  H   C(CH.sub.3).sub.3                                                                         CH.sub.3                                                                             CH.sub.3                                                                             O  193-195°                               2  H   C(CH.sub.3).sub.3                                                                         OCH.sub.3                                                                            CH.sub.3                                                                             O  175-179°                               2  H   C(CH.sub.3 ).sub.3                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                            O  178-181°                               2  3-NH.sub.2                                                                         CH.sub.2 CHCH.sub.2                                                                       CH.sub.3                                                                             CH.sub.3                                                                             S                                                0  6-F CHCHC.sub.2 H.sub.5                                                                       CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                            S                                                0  3-Br                                                                               CH.sub.2 CH.sub.2 CHCH.sub.2                                                              C.sub.2 H.sub.5                                                                      CH.sub.3                                                                             S                                                0  5-Cl                                                                                ##STR35## CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                                                             S                                                0  6-CH.sub.3                                                                          ##STR36## OC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                            S                                                0  H    -n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                      CH.sub.3                                                                             O                                                0  H    -n-C.sub.3 H.sub.7                                                                       OC.sub.2 H.sub.5                                                                     CH.sub.3                                                                             O                                                0  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                                                             O                                                0  H    -n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                            O                                                0  H    -n-C.sub.3 H.sub.7                                                                       OC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                            O                                                0  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                            O                                                2  H    -n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                      CH.sub.3                                                                             O                                                2  H    -n-C.sub.3 H.sub.7                                                                       OC.sub.2 H.sub.5                                                                     CH.sub.3                                                                             O                                                2  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                                                             O                                                2  H    -n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                            O                                                2  H    -n-C.sub.3 H.sub.7                                                                       OC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                            O                                                2  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                            O                                                2  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             CH.sub.3                                                                             S                                                2  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            S                                                2  H    -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            S                                                0  H   CH(CH.sub.3).sub.2                                                                        C.sub.2 H.sub.5                                                                      CH.sub.3                                                                             O                                                0  H   CH(CH.sub.3).sub.2                                                                        OC.sub.2 H.sub.5                                                                     CH.sub.3                                                                             O                                                0  H   CH(CH.sub.3).sub.2                                                                        CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                                                             O                                                0  H   CH(CH.sub.3).sub.2                                                                        C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                            O                                                0  H   CH(CH.sub.3).sub.2                                                                        OC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                            O                                                0  H   CH(CH.sub.3).sub.2                                                                        CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                            O                                                2  H   CH(CH.sub.3).sub.2                                                                        C.sub.2 H.sub.5                                                                      CH.sub.3                                                                             O                                                2  H   CH(CH.sub.3).sub.2                                                                        OC.sub.2 H.sub.5                                                                     CH.sub.3                                                                             O                                                2  H   CH(CH.sub.3).sub.2                                                                        CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                                                             O                                                2  H   CH(CH.sub.3).sub.2                                                                        C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                            O                                                2  H   CH(CH.sub.3).sub.2                                                                        OCH.sub.2 H.sub.5                                                                    OCH.sub.3                                                                            O                                                2  H   CH(CH.sub.3).sub.2                                                                        CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                            O                                                2  H   CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                             CH.sub.3                                                                             S                                                2  H   CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                             OCH.sub.3                                                                            S                                                2  H   CH(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                            S                                                0  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             CH.sub.3                                                                             O  150-157°                               0  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            O  128-135°                               0  H     -n-C.sub.3 H.sub.7                                                                      OCH.sub.3                                                                            OCH.sub.3                                                                            O  152-155°                               1  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             CH.sub.3                                                                             O  163-166°                               1  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            O   75-95°                                1  H    -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O  122-125°                               0  H   CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                             CH.sub.3                                                                             O                                                0  H   CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                             OCH.sub.3                                                                            O                                                0  H   CH(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                1  H   CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                             CH.sub.3                                                                             O                                                1  H   CH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                             OCH.sub.3                                                                            O                                                1  H   CH(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                0  H                                                                                   ##STR37## CH.sub.3                                                                             CH.sub.3                                                                             O                                                0  H                                                                                   ##STR38## CH.sub.3                                                                             OCH.sub.3                                                                            O                                                0  H                                                                                   ##STR39## OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  H                                                                                   ##STR40## CH.sub.3                                                                             CH.sub.3                                                                             O  138-140°                               2  H                                                                                   ##STR41## CH.sub.3                                                                             OCH.sub.3                                                                            O  188-190°                               2  H                                                                                   ##STR42## OCH.sub.3                                                                            OCH.sub.3                                                                            O  211-212°                               0  H   CH.sub.2 CHCH.sub.2                                                                       CH.sub.3                                                                             CH.sub.3                                                                             O  150-158°                               0  H   CH.sub.2 CHCH.sub.2                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            O  130-135°                               0  H   CH.sub.2 CHCH.sub.2                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O  125-130°                               2  H   CH.sub.2 CHCH.sub.2                                                                       CH.sub.3                                                                             CH.sub.3                                                                             O  185-190°                               2  H   CH.sub.2 CHCH.sub.2                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            O  188-190°                               2  H   CH.sub.2 CHCH.sub.2                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O  187-190°                               2  H   CH(CH.sub. 3)CHCH.sub.2                                                                   CH.sub.3                                                                             CH.sub.3                                                                             O                                                2  H   CH(CH.sub.3)CHCH.sub.2                                                                    CH.sub.3                                                                             OCH.sub.3                                                                            O                                                2  H   CH(CH.sub.3)CHCH.sub.2                                                                    OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  H   CH.sub.2 CH.sub.2 CHCH.sub.2                                                              CH.sub.3                                                                             CH.sub.3                                                                             O                                                2  H   CH.sub.2 CH.sub.2 CHCH.sub.2                                                              CH.sub.3                                                                             OCH.sub.3                                                                            O                                                2  H   CH.sub.2 CH.sub.2 CHCH.sub.2                                                              OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                0  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             CH.sub.3                                                                             S                                                0  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            S                                                0  H    -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            S                                                0  H   CH.sub.2 CHCH.sub.2                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            S                                                2  H   CHCHCH.sub.3                                                                              CH.sub.3                                                                             OCH.sub.3                                                                            O                                                2  H   CHCHCH.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             OCH.sub.3                                                                            O                                                2  H   CH.sub.2 CH.sub.2 CHCH.sub.2                                                              OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  H   CH.sub.2 CHCHCH.sub.3                                                                     OCH.sub.3                                                                            CH.sub.3                                                                             O                                                2  3-F  -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            O                                                2  6-F  -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             CH.sub.3                                                                             O                                                2  3-NO.sub.2                                                                          -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  5-Cl                                                                                -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            CH.sub.3                                                                             O                                                2  6-Cl                                                                                -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  3-Br                                                                                -n-C.sub.4 H.sub.9                                                                       OCH.sub.3                                                                            CH.sub.3                                                                             O                                                2  5-Br                                                                                -n-C.sub.4 H.sub.9                                                                       OCH.sub.3                                                                            CH.sub.3                                                                             O                                                2  3-CH.sub.3                                                                          -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             OCH.sub.2 CH.sub.3                                                                   O                                                2  5-NO.sub.2                                                                          -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            O                                                2  5-CH.sub.3                                                                          -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  6-CH.sub.3                                                                          -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  3-CF.sub.3                                                                          -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            CH.sub.3                                                                             O                                                2  6-NO.sub.2                                                                          -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            O                                                2  5-CF.sub.3                                                                          -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            O                                                2  6-CF.sub.3                                                                          -n-C.sub.3 H.sub.7                                                                       CH.sub.3                                                                             CH.sub.3                                                                             O                                                2  3-CN                                                                                -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  5-CN                                                                                -n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                2  H    -n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                            O                                                2  H    -n-C.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                      CH.sub.3                                                                             O                                                2  H    -n-C.sub.3 H.sub.7                                                                       OC.sub.2 H.sub.5                                                                     CH.sub.3                                                                             O                                                2  H    -n-C.sub.3 H.sub.7                                                                       OC.sub.2 H.sub.5                                                                     OCH.sub.3                                                                            O                                                2  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                                                             O                                                2  H    -n-C.sub.3 H.sub.7                                                                       CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                            O                                                1  H   CH.sub.2 CHCH.sub.2                                                                       CH.sub.3                                                                             CH.sub.3                                                                             O                                                1  H   CH.sub.2 CHCH.sub.2                                                                       CH.sub.3                                                                             OCH.sub.3                                                                            O                                                1  H   CH.sub.2 CHCH.sub.2                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                            O                                                __________________________________________________________________________

                  TABLE III                                                        ______________________________________                                          ##STR43##                                                                     R.sub.1       R.sub.2   Q        m.p. (°C.)                             ______________________________________                                         SCH.sub.2 CH.sub.2 CH.sub.3                                                                  H         NH.sub.2  58-64°                                SCH.sub.2 CH.sub.2 CH.sub.3                                                                  3-Cl      NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                  5-Cl      NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                  6-Cl      NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                  3-CH.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                  5-CH.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                  6-CH.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                  3-OCH.sub.3                                                                              NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                  5-OCH.sub.3                                                                              NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                  6-OCH.sub.3                                                                              NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                  3-CF.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                  5-CF.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                  6-CF.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                  5-F       NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                  5-Br      NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                  5-NO.sub.2                                                                               NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                  5-CN      NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          H         NH.sub.2 122-124°                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          3-Cl      NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          5-Cl      NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          6-Cl      NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          3-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          5-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          6-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          3-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          5-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          6-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          3-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          5-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          6-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          5-F       NH.sub.2                                               SO.sub. 2 CH.sub.2 CH.sub.2 CH.sub.3                                                         5-Br      NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          5-NO.sub.2                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          5-CN      NH.sub.2                                               SCH(CH.sub.3).sub.2                                                                          H         NH.sub.2 oil (IR: 3200                                                                  and 3300 cm.sup.-1)                           SCH(CH.sub.3).sub.2                                                                          3-Cl      NH.sub.2                                               SCH(CH.sub.3).sub.2                                                                          5-Cl      NH.sub.2                                               SCH(CH.sub.3).sub.2                                                                          6-Cl      NH.sub.2                                               SCH(CH.sub.3).sub.2                                                                          3-CH.sub.3                                                                               NH.sub.2                                               SCH(CH.sub.3).sub.2                                                                          5-CH.sub.3                                                                               NH.sub.2                                               SCH(CH.sub.3).sub.2                                                                          6-CH.sub.3                                                                               NH.sub.2                                               SCH(CH.sub.3).sub.2                                                                          3-OCH.sub.3                                                                              NH.sub.2                                               SCH(CH.sub.3).sub.2                                                                          5-OCH.sub.3                                                                              NH.sub.2                                               SCH(CH.sub.3).sub.2                                                                          6-OCH.sub.3                                                                              NH.sub.2                                               SCH(CH.sub.3).sub.2                                                                          3-CF.sub.3                                                                               NH.sub.2                                               SCH(CH.sub.3).sub.2                                                                          5-CF.sub.3                                                                               NH.sub.2                                               SCH(CH.sub.3).sub.2                                                                          6-CF.sub.3                                                                               NH.sub.2                                               SCH(CH.sub.3).sub.2                                                                          5-F       NH.sub.2                                               SCH(CH.sub.3).sub.2                                                                          5-Br      NH.sub.2                                               SCH(CH.sub.3).sub.2                                                                          5-NO.sub.2                                                                               NH.sub.2                                               SCH(CH.sub.3).sub.2                                                                          5-CN      NH.sub.2                                               SO.sub.2 CH(CH.sub.3).sub.2                                                                  H         NH.sub.2 149-153°                               SO.sub.2 CH(CH.sub.3).sub.2                                                                  3-Cl      NH.sub.2                                               SO.sub.2 CH(CH.sub.3).sub. 2                                                                 5-Cl      NH.sub.2                                               SO.sub.2 CH(CH.sub.3).sub.2                                                                  6-Cl      NH.sub.2                                               SO.sub.2 CH(CH.sub.3).sub.2                                                                  3-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH(CH.sub.3).sub.2                                                                  5-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH(CH.sub.3).sub.2                                                                  6-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH(CH.sub.3).sub.2                                                                  3-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 CH(CH.sub.3).sub.2                                                                  5-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 CH(CH.sub.3).sub.2                                                                  6-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 CH(CH.sub.3).sub.2                                                                  3-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH(CH.sub.3).sub.2                                                                  5-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH(CH.sub.3).sub.2                                                                  6-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH(CH.sub.3).sub.2                                                                  5-F       NH.sub.2                                               SO.sub.2 CH(CH.sub.3).sub.2                                                                  5-Br      NH.sub.2                                               SO.sub.2 CH(CH.sub.3).sub.2                                                                  5-NO.sub.2                                                                               NH.sub.2                                               SO.sub.2 CH(CH.sub.3).sub.2                                                                  5-CN      NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         H         NH.sub.2  65-70°                                SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         3-Cl      NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         5-Cl      NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         6-Cl      NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         3-CH.sub.3 CH                                                                            NH.sub. 2                                              SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         5-CH.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         6-CH.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         3-OCH.sub.3                                                                              NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         5-OCH.sub.3                                                                              NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         6-OCH.sub.3                                                                              NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         3-CF.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         5-CF.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         6-CF.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         5-F       NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         5-Br      NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         5-NO.sub.2                                                                               NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         5-CN      NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 H         NH.sub.2 136-138°                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 3-Cl      NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 5-Cl      NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 6-Cl      NH.sub.2                                               SO.sub.2 CH.sub. 2 CH.sub.2 CH.sub.2 CH.sub.3                                                3-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 5-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 6-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 3-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 5-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 6-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 3-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 5-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 6-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 5-F       NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 5-Br      NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 5-NO.sub.2                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 5-CN      NH.sub.2                                               SCH.sub.2 CH(CH.sub.3).sub.2                                                                 H         NH.sub.2  66-76°                                SCH.sub.2 CH(CH.sub.3).sub.2                                                                 3-Cl      NH.sub.2                                               SCH.sub.2 CH(CH.sub.3).sub.2                                                                 5-Cl      NH.sub.2                                               SCH.sub.2 CH(CH.sub.3).sub.2                                                                 6-Cl      NH.sub.2                                               SCH.sub.2 CH(CH.sub.3).sub.2                                                                 3-CH.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CH(CH.sub.3).sub.2                                                                 5-CH.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CH(CH.sub.3).sub.2                                                                 6-CH.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CH(CH.sub.3).sub.2                                                                 3-OCH.sub.3                                                                              NH.sub.2                                               SCH.sub.2 CH(CH.sub.3).sub.2                                                                 5-OCH.sub.3                                                                              NH.sub.2                                               SCH.sub.2 CH(CH.sub.3).sub.2                                                                 6-OCH.sub.3                                                                              NH.sub.2                                               SCH.sub.2 CH(CH.sub.3).sub.2                                                                 3-CF.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CH(CH.sub.3).sub.2                                                                 5-CF.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CH(CH.sub.3).sub.2                                                                 6-CF.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CH(CH.sub.3).sub.2                                                                 5-F       NH.sub.2                                               SCH.sub.2 CH(CH.sub.3).sub.2                                                                 5-Br      NH.sub.2                                               SCH.sub.2 CH(CH.sub.3).sub.2                                                                 5-NO.sub.2                                                                               NH.sub.2                                               SCH.sub.2 CH(CH.sub.3).sub.2                                                                 5-CN      NH.sub.2                                               SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         H         NH.sub.2 125-127°                               SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         3-Cl      NH.sub.2                                               SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         5-Cl      NH.sub.2                                               SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         6-Cl      NH.sub.2                                               SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         3-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         5-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         6-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         3-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         5-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         6-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         3-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         5-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         6-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         5-F       NH.sub.2                                               SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         5-Br      NH.sub.2                                               SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         5-NO.sub.2                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         5-CN      NH.sub.2                                               SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               H         NH.sub.2                                               SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               3-Cl      NH.sub.2                                               SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               5-Cl      NH.sub.2                                               SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               6-Cl      NH.sub.2                                               SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               3-CH.sub.3                                                                               NH.sub.2                                               SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               5-CH.sub.3                                                                               NH.sub.2                                               SCH(CH.sub. 3)CH.sub.2 CH.sub.3                                                              6-CH.sub.3                                                                               NH.sub.2                                               SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               3-OCH.sub.3                                                                              NH.sub.2                                               SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               5-OCH.sub.3                                                                              NH.sub.2                                               SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               6-OCH.sub.3                                                                              NH.sub.2                                               SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               3-CF.sub.3                                                                               NH.sub.2                                               SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               5-CF.sub.3                                                                               NH.sub.2                                               SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               6-CF.sub.3                                                                               NH.sub.2                                               SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               5-F       NH.sub.2                                               SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               5-Br      NH.sub.2                                               SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               5-NO.sub.2                                                                               NH.sub.2                                               SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               5-CN      NH.sub.2                                               SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       H         NH.sub.2 150-168°                               SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       3-Cl      NH.sub.2                                               SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       5-Cl      NH.sub.2                                               SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       6-Cl      NH.sub.2                                               SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       3-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       5-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       6-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       3-OCH.sub.3                                                                              NH.sub. 2                                              SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       5-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       6-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       3-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       5-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       6-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       5-F       NH.sub.2                                               SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       5-Br      NH.sub.2                                               SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       5-NO.sub.2                                                                               NH.sub.2                                               SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       5-CN      NH.sub.2                                                ##STR44##    H         NH.sub.2                                                ##STR45##    3-Cl      NH.sub.2                                                ##STR46##    5-Cl      NH.sub.2                                                ##STR47##    6-Cl      NH.sub.2                                                ##STR48##    3-CH.sub.3                                                                               NH.sub.2                                                ##STR49##    5-CH.sub.3                                                                               NH.sub.2                                                ##STR50##    6-CH.sub.3                                                                               NH.sub.2                                                ##STR51##    3-OCH.sub.3                                                                              NH.sub.2                                                ##STR52##    5-OCH.sub.3                                                                              NH.sub.2                                                ##STR53##    6-OCH.sub.3                                                                              NH.sub.2                                                ##STR54##    3-CF.sub.3                                                                               NH.sub.2                                                ##STR55##    5-CF.sub.3                                                                               NH.sub.2                                                ##STR56##    6-CF.sub.3                                                                               NH.sub.2                                                ##STR57##    5-F       NH.sub.2                                                ##STR58##    5-Br      NH.sub.2                                                ##STR59##    5-NO.sub.2                                                                               NH.sub.2                                                ##STR60##    5-CN      NH.sub.2                                                ##STR61##    H         NH.sub.2                                                ##STR62##    3-Cl      NH.sub.2                                                ##STR63##    5-Cl      NH.sub.2                                                ##STR64##    6-Cl      NH.sub.2                                                ##STR65##    3-CH.sub.3                                                                               NH.sub.2                                                ##STR66##    5-CH.sub.3                                                                               NH.sub.2                                                ##STR67##    6-CH.sub.3                                                                               NH.sub.2                                                ##STR68##    3-OCH.sub.3                                                                              NH.sub.2                                                ##STR69##    5-OCH.sub.3                                                                              NH.sub.2                                                ##STR70##    6-OCH.sub.3                                                                              NH.sub.2                                                ##STR71##    3-CF.sub.3                                                                               NH.sub.2                                                ##STR72##    5-CF.sub.3                                                                               NH.sub.2                                                ##STR73##    6-CF.sub.3                                                                               NH.sub.2                                                ##STR74##    5-F       NH.sub.2                                                ##STR75##    5-Br      NH.sub.2                                                ##STR76##    5-NO.sub.2                                                                               NH.sub.2                                                ##STR77##    5-CN      NH.sub.2                                               SCH.sub.2 CHCH.sub.2                                                                         H         NH.sub.2  49-52°                                SCH.sub.2 CHCH.sub.2                                                                         3-Cl      NH.sub.2                                               SCH.sub.2 CHCH.sub.2                                                                         5-Cl      NH.sub.2                                               SCH.sub.2 CHCH.sub.2                                                                         6-Cl      NH.sub.2                                               SCH.sub.2 CHCH.sub.2                                                                         3-CH.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CHCH.sub.2                                                                         5-CH.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CHCH.sub.2                                                                         6-CH.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CH CH.sub.2                                                                        3-OCH.sub.3                                                                              NH.sub.2                                               SCH.sub.2 CHCH.sub.2                                                                         5-OCH.sub.3                                                                              NH.sub.2                                               SCH.sub.2 CHCH.sub.2                                                                         6-OCH.sub.3                                                                              NH.sub.2                                               SCH.sub.2 CHCH.sub.2                                                                         3-CF.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CHCH.sub.2                                                                         5-CF.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CHCH.sub.2                                                                         6-CF.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CHCH.sub.2                                                                         5-F       NH.sub.2                                               SCH.sub.2 CHCH.sub.2                                                                         5-Br      NH.sub.2                                               SCH.sub.2 CHCH.sub.2                                                                         5-NO.sub.2                                                                               NH.sub.2                                               SCH.sub.2 CHCH.sub.2                                                                         5-CN      NH.sub.2                                               SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 H         NH.sub.2 126-128°                               SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 3-Cl      NH.sub.2                                               SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 5-Cl      NH.sub.2                                               SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 6-Cl      NH.sub.2                                               SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 3-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 5-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 6-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 3-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 5-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 6-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 3-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 5-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 6-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 5-F       NH.sub.2                                               SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 5-Br      NH.sub.2                                               SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 5-NO.sub.2                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 5-CN      NH.sub.2                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                  H         NCO      oil                                           SCH.sub.2 CH.sub.2 CH.sub.3                                                                  3-Cl      NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.3                                                                  5-Cl      NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.3                                                                  6-Cl      NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.3                                                                  3-CH.sub.3                                                                               NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.3                                                                  5-CH.sub.3                                                                               NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.3                                                                  6-CH.sub.3                                                                               NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.3                                                                  3-OCH.sub.3                                                                              NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.3                                                                  5-OCH.sub.3                                                                              NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.3                                                                  6-OCH.sub.3                                                                              NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.3                                                                  3-CF.sub.3                                                                               NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.3                                                                  5-CF.sub.3                                                                               NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.3                                                                  6-CF.sub.3                                                                               NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.3                                                                  5-F       NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.3                                                                  5-Br      NCO                                                    SCH.sub.2 CH.sub.2 CH.sub. 3                                                                 5-NO.sub.2                                                                               NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.3                                                                  5-CN      NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          H         NCO      oil (IR: 2230                                                                  cm.sup.-1)                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          3-Cl      NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          5-Cl      NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          6-Cl      NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          3-CH.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          5-CH.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          6-CH.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          3-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          5-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          6-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          3-CF.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          5-CF.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          6-CF.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          5-F       NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          5-Br      NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          5-NO.sub.2                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          5-CN      NCO                                                    SCH(CH.sub.3).sub.2                                                                          H         NCO                                                    SCH(CH.sub.3).sub.2                                                                          3-Cl      NCO                                                    SCH(CH.sub.3).sub.2                                                                          5-Cl      NCO                                                    SCH(CH.sub.3).sub.2                                                                          6-Cl      NCO                                                    SCH(CH.sub.3).sub.2                                                                          3-CH.sub.3                                                                               NCO                                                    SCH(CH.sub.3).sub.2                                                                          5-CH.sub.3                                                                               NCO                                                    SCH(CH.sub.3).sub.2                                                                          6-CH.sub.3                                                                               NCO                                                    SCH(CH.sub.3).sub.2                                                                          3-OCH.sub.3                                                                              NCO                                                    SCH(CH.sub.3).sub.2                                                                          5-OCH.sub.3                                                                              NCO                                                    SCH(CH.sub.3).sub.2                                                                          6-OCH.sub.3                                                                              NCO                                                    SCH(CH.sub.3).sub.2                                                                          3-CF.sub.3                                                                               NCO                                                    SCH(CH.sub.3).sub.2                                                                          5-CF.sub.3                                                                               NCO                                                    SCH(CH.sub.3).sub.2                                                                          6-CF.sub.3                                                                               NCO                                                    SCH(CH.sub.3).sub.2                                                                          5-F       NCO                                                    SCH(CH.sub.3).sub.2                                                                          5-Br      NCO                                                    SCH(CH.sub.3).sub.2                                                                          5-NO.sub.2                                                                               NCO                                                    SCH(CH.sub.3).sub.2                                                                          5-CN      NCO                                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                  H         NCO      oil (IR: 2200                                                                  cm.sup.-1)                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                  3-Cl      NCO                                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                  5-Cl      NCO                                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                  6-Cl      NCO                                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                  3-CH.sub.3                                                                               NCO                                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                  5-CH.sub.3                                                                               NCO                                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                  6-CH.sub.3                                                                               NCO                                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                  3-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                  5-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                  6-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                  3-CF.sub.3                                                                               NCO                                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                  5-CF.sub.3                                                                               NCO                                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                  6-CF.sub.3                                                                               NCO                                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                  5-F       NCO                                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                  5-Br      NCO                                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                  5-NO.sub.2                                                                               NCO                                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                  5-CN      NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         H         NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         3-Cl      NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         5-Cl      NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         6-Cl      NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         3-CH.sub.3 CH                                                                            NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         5-CH.sub.3                                                                               NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         6-CH.sub.3                                                                               NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         3-OCH.sub.3                                                                              NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         5-OCH.sub.3                                                                              NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         6-OCH.sub.3                                                                              NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         3-CF.sub.3                                                                               NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         5-CF.sub.3                                                                               NCO                                                    SCH.sub. 2 CH.sub.2 CH.sub.2 CH.sub.3                                                        6-CF.sub.3                                                                               NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         5-F       NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         5-Br      NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         5-NO.sub.2                                                                               NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         5-CN      NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 H         NCO      oil                                           SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 3-Cl      NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 5-Cl      NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 6-Cl      NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 3-CH.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 5-CH.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 6-CH.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 3-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 5-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 6-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 3-CF.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 5-CF.sub. 3                                                                              NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 6-CF.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 5-F       NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 5-Br      NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 5-NO.sub.2                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                 5-CN      NCO                                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                 H         NCO                                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                 3-Cl      NCO                                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                 5-Cl      NCO                                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                 6-Cl      NCO                                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                 3-CH.sub.3                                                                               NCO                                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                 5-CH.sub.3                                                                               NCO                                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                 6-CH.sub.3                                                                               NCO                                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                 3-OCH.sub.3                                                                              NCO                                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                 5-OCH.sub.3                                                                              NCO                                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                 6-OCH.sub.3                                                                              NCO                                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                 3-CF.sub.3                                                                               NCO                                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                 5-CF.sub.3                                                                               NCO                                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                 6-CF.sub.3                                                                               NCO                                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                 5-F       NCO                                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                 5-Br      NCO                                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                 5-NO.sub. 2                                                                              NCO                                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                 5-CN      NCO                                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         H         NCO      oil                                           SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         3-Cl      NCO                                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         5-Cl      NCO                                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         6-Cl      NCO                                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         3-CH.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         5-CH.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         6-CH.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         3-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         5-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         6-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         3-CF.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         5-CF.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         6-CF.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         5-F       NCO                                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         5-Br      NCO                                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         5-NO.sub.2                                                                               NCO                                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         5-CN      NCO                                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               H         NCO                                                    SCH(CH.sub.3 )CH.sub.2 CH.sub.3                                                              3-Cl      NCO                                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               5-Cl      NCO                                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               6-Cl      NCO                                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               3-CH.sub.3                                                                               NCO                                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               5-CH.sub.3                                                                               NCO                                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               6-CH.sub.3                                                                               NCO                                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               3-OCH.sub.3                                                                              NCO                                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               5-OCH.sub.3                                                                              NCO                                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               6-OCH.sub.3                                                                              NCO                                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               3-CF.sub.3                                                                               NCO                                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               5-CF.sub.3                                                                               NCO                                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               6-CF.sub.3                                                                               NCO                                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               5-F       NCO                                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               5-Br      NCO                                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               5-NO.sub.2                                                                               NCO                                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                               5-CN      NCO                                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       H         NCO      oil                                           SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       3-Cl      NCO                                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       5-Cl      NCO                                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       6-Cl      NCO                                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       3-CH.sub.3                                                                               NCO                                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       5-CH.sub.3                                                                               NCO                                                    SO.sub. 2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      6-CH.sub.3                                                                               NCO                                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       3-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       5-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       6-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       3-CF.sub.3                                                                               NCO                                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       5-CF.sub.3                                                                               NCO                                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       6-CF.sub.3                                                                               NCO                                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       5-F       NCO                                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       5-Br      NCO                                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       5-NO.sub.2                                                                               NCO                                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                       5-CN      NCO                                                     ##STR78##    H         NCO                                                     ##STR79##    3-Cl      NCO                                                     ##STR80##    5-Cl      NCO                                                     ##STR81##    6-Cl      NCO                                                     ##STR82##    3-CH.sub.3                                                                               NCO                                                     ##STR83##    5-CH.sub.3                                                                               NCO                                                     ##STR84##    6-CH.sub.3                                                                               NCO                                                     ##STR85##    3-OCH.sub.3                                                                              NCO                                                     ##STR86##    5-OCH.sub.3                                                                              NCO                                                     ##STR87##    3-CF.sub.3                                                                               NCO                                                     ##STR88##    3-CF.sub.3                                                                               NCO                                                     ##STR89##    5-CF.sub.3                                                                               NCO                                                     ##STR90##    6-CF.sub.3                                                                               NCO                                                     ##STR91##    5-F       NCO                                                     ##STR92##    5-Br      NCO                                                     ##STR93##    5-NO.sub.2                                                                               NCO                                                     ##STR94##    5-CN      NCO                                                     ##STR95##    H         NCO      oil (IR: 2250 cm.sup.-1)                       ##STR96##    3-Cl      NCO                                                     ##STR97##    5-Cl      NCO                                                     ##STR98##    6-Cl      NCO                                                     ##STR99##    3-CH.sub.3                                                                               NCO                                                     ##STR100##   5-CH.sub.3                                                                               NCO                                                     ##STR101##   6-CH.sub.3                                                                               NCO                                                     ##STR102##   3-OCH.sub.3                                                                              NCO                                                     ##STR103##   5-OCH.sub.3                                                                              NCO                                                     ##STR104##   6-OCH.sub.3                                                                              NCO                                                     ##STR105##   3-CF.sub.3                                                                               NCO                                                     ##STR106##   5-CF.sub.3                                                                               NCO                                                     ##STR107##   6-CF.sub.3                                                                               NCO                                                     ##STR108##   5-F       NCO                                                     ##STR109##   5-Br      NCO                                                     ##STR110##   5-NO.sub.2                                                                               NCO                                                     ##STR111##   5-CN      NCO                                                    SCH.sub.2 CHCH.sub.2                                                                         H         NCO                                                    SCH.sub.2 CHCH.sub.2                                                                         3-Cl      NCO                                                    SCH.sub.2 CHCH.sub.2                                                                         5-Cl      NCO                                                    SCH.sub.2 CHCH.sub.2                                                                         6-Cl      NCO                                                    SCH.sub.2 CHCH.sub.2                                                                         3-CH.sub.3                                                                               NCO                                                    SCH.sub.2 CHCH.sub.2                                                                         5-CH.sub.3                                                                               NCO                                                    SCH.sub.2 CHCH.sub.2                                                                         6-CH.sub.3                                                                               NCO                                                    SCH.sub.2 CHCH.sub.2                                                                         3-OCH.sub.3                                                                              NCO                                                    SCH.sub.2 CHCH.sub.2                                                                         5-OCH.sub.3                                                                              NCO                                                    SCH.sub.2 CHCH.sub.2                                                                         6-OCH.sub.3                                                                              NCO                                                    SCH.sub.2 CHCH.sub. 2                                                                        3-CF.sub.3                                                                               NCO                                                    SCH.sub.2 CHCH.sub.2                                                                         5-CF.sub.3                                                                               NCO                                                    SCH.sub.2 CHCH.sub.2                                                                         6-CF.sub.3                                                                               NCO                                                    SCH.sub.2 CHCH.sub.2                                                                         5-F       NCO                                                    SCH.sub.2 CHCH.sub.2                                                                         5-Br      NCO                                                    SCH.sub.2 CHCH.sub.2                                                                         5-NO.sub.2                                                                               NCO                                                    SCH.sub.2 CHCH.sub.2                                                                         5-CN      NCO                                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 H         NCO                                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 3-Cl      NCO                                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 5-Cl      NCO                                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 6-Cl      NCO                                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 3-CH.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 5-CH.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 6-CH.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 3-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 5-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 6-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 3-CF.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 5-CF.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 6-CF.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 5-F       NCO                                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 5-Br      NCO                                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 5-NO.sub.2                                                                               NCO                                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                 5-CN      NCO                                                    SCH.sub.2 CHCHCH.sub.3                                                                       H         NH.sub.2                                               SCH.sub.2 CHCHCH.sub.3                                                                       5-Cl      NH.sub.2                                               SCH.sub.2 CHCHCH.sub.3                                                                       5-CH.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CHCHCH.sub.3                                                                       5-CF.sub.3                                                                               NH.sub.2                                               SCH.sub.2 CHCHCH.sub.3                                                                       5-OCH.sub.3                                                                              NH.sub.2                                               SCH.sub.2 CHCHCH.sub.3                                                                       5-F       NH.sub.2                                               SCH.sub.2 CHCHCH.sub.3                                                                       5-Br      NH.sub.2                                               SCH.sub.2 CHCHCH.sub.3                                                                       5-NO.sub.2                                                                               NH.sub.2                                               SCH.sub.2 CHCHCH.sub.3                                                                       5-CN      NH.sub.2                                               SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               H         NH.sub.2                                               SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               5-Cl      NH.sub.2                                               SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               5-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               5-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               5-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               5-F       NH.sub.2                                               SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               5-Br      NH.sub.2                                               SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               5-NO.sub.2                                                                               NH.sub.2                                               SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               5-CN      NH.sub.2                                               SCH.sub.2 CHCHCH.sub.3                                                                       H         NCO                                                    SCH.sub.2 CHCHCH.sub.3                                                                       5-Cl      NCO                                                    SCH.sub.2 CHCHCH.sub. 3                                                                      5-CH.sub.3                                                                               NCO                                                    SCH.sub.2 CHCHCH.sub.3                                                                       5-CF.sub.3                                                                               NCO                                                    SCH.sub.2 CHCHCH.sub.3                                                                       5-OCH.sub.3                                                                              NCO                                                    SCH.sub.2 CHCHCH.sub.3                                                                       5-F       NCO                                                    SCH.sub.2 CHCHCH.sub.3                                                                       5-Br      NCO                                                    SCH.sub.2 CHCHCH.sub.3                                                                       5-NO.sub.2                                                                               NCO                                                    SCH.sub.2 CHCHCH.sub.3                                                                       5-CN      NCO                                                    SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               H         NCO                                                    SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               5-Cl      NCO                                                    SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               5-CH.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               5-CF.sub.3                                                                               NCO                                                    SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               5-OCH.sub.3                                                                              NCO                                                    SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               5-F       NCO                                                    SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               5-Br      NCO                                                    SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               5-NO.sub.2                                                                               NCO                                                    SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               5-CN      NCO                                                    SC(CH.sub.3).sub.3                                                                           H         NH.sub.2                                               SC(CH.sub.3).sub.3                                                                           5-Cl      NH.sub.2                                               SC(CH.sub.3).sub.3                                                                           5-CH.sub.3                                                                               NH.sub.2                                               SC(CH.sub.3).sub.3                                                                           5-CF.sub.3                                                                               NH.sub.2                                               SC(CH.sub.3).sub.3                                                                           5-OCH.sub.3                                                                              NH.sub.2                                               SC(CH.sub.3).sub.3                                                                           5-F       NH.sub.2                                               SC(CH.sub.3).sub.3                                                                           5-Br      NH.sub.2                                               SC(CH.sub.3).sub.3                                                                           5-NO.sub.2                                                                               NH.sub.2                                               SC(CH.sub.3).sub.3                                                                           5-CN      NH.sub. 2                                              SO.sub.2 C(CH.sub.3).sub.3                                                                   H         NH.sub.2 134-142°                               SO.sub.2 C(CH.sub.3).sub.3                                                                   5-Cl      NH.sub.2                                               SO.sub.2 C(CH.sub.3).sub.3                                                                   5-CH.sub.3                                                                               NH.sub.2                                               SO.sub.2 C(CH.sub.3).sub.3                                                                   5-CF.sub.3                                                                               NH.sub.2                                               SO.sub.2 C(CH.sub.3).sub.3                                                                   5-OCH.sub.3                                                                              NH.sub.2                                               SO.sub.2 C(CH.sub.3).sub.3                                                                   5-F       NH.sub.2                                               SO.sub.2 C(CH.sub.3).sub.3                                                                   5-Br      NH.sub.2                                               SO.sub.2 C(CH.sub.3).sub.3                                                                   5-NO.sub.2                                                                               NH.sub.2                                               SO.sub.2 C(CH.sub.3).sub.3                                                                   5-CN      NH.sub.2                                               SC(CH.sub.3).sub.3                                                                           H         NCO                                                    SC(CH.sub.3).sub.3                                                                           5-Cl      NCO                                                    SC(CH.sub.3).sub.3                                                                           5-CH.sub.3                                                                               NCO                                                    SC(CH.sub.3).sub.3                                                                           5-CF.sub.3                                                                               NCO                                                    SC(CH.sub.3).sub.3                                                                           5-OCH.sub.3                                                                              NCO                                                    SC(CH.sub.3).sub.3                                                                           5-F       NCO                                                    SC(CH.sub.3).sub.3                                                                           5-Br      NCO                                                    SC(CH.sub.3).sub.3                                                                           5-NO.sub.2                                                                               NCO                                                    SC(CH.sub.3).sub.3                                                                           5-CN      NCO                                                    SO.sub.2 C(CH.sub.3).sub.3                                                                   H         NCO      oil                                           SO.sub.2 C(CH.sub.3).sub.3                                                                   5-Cl      NCO                                                    SO.sub.2 C(CH.sub.3).sub.3                                                                   5-CH.sub.3                                                                               NCO                                                    SO.sub.2 C(CH.sub.3).sub.3                                                                   5-CF.sub.3                                                                               NCO                                                    SO.sub.2 C(CH.sub.3).sub.3                                                                   5-OCH.sub.3                                                                              NCO                                                    SO.sub.2 C(CH.sub.3).sub.3                                                                   5-F       NCO                                                    SO.sub.2 C(CH.sub.3).sub.3                                                                   5-Br      NCO                                                    SO.sub.2 C(CH.sub.3).sub.3                                                                   5-NO.sub.2                                                                               NCO                                                    SO.sub.2 C(CH.sub.3).sub.3                                                                   5-CN      NCO                                                    SCH.sub.2 CH.sub.2 CH.sub.3                                                                  H         NCS                                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          H         NCS                                                    SCH(CH.sub.3).sub.2                                                                          H         NCS                                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                  H         NCS                                                    ______________________________________                                    

FORMULATIONS

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

                  TABLE IV                                                         ______________________________________                                                     Active  Weight Percent*                                                        Ingredient                                                                             Di1uent(s)                                                                               Surfactant(s)                                    ______________________________________                                         Wettable Powders                                                                             20-90      0-74     1-10                                         Oil Suspensions,                                                                              3-50     40.95     0-15                                         Emulsions, Solutions,                                                          (including Emulsifiable                                                        Concentrates)                                                                  Aqueous Suspension                                                                           10-50     40-84     1-20                                         Dusts          1-25     70-99     0-5                                          Granules and Pellets                                                                         0.1-95      5-99.9  0-15                                         High Strength 90-99     0-10      0-2                                          Compositions                                                                   ______________________________________                                          *Active ingredient plus at 1east one of a Surfactant or a Diluent equals       100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc., New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

EXAMPLE 10

    ______________________________________                                         Wettable Powder                                                                ______________________________________                                         N--[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-                                                      80%                                              [(1-methylethyl)sulfony1]benzenesulfonamide                                    sodium alkylnaphthalenesulfonate                                                                              2%                                              sodium ligninsulfonate         2%                                              synthetic amorphous silica     3%                                              kaolinite                     13%                                              ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.

EXAMPLE 11

    ______________________________________                                         Wettable Powder                                                                ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-[(1-                                                      50%                                               methylethyl)sulfonyl]benzenesulfonamide                                        sodium alkylnaphthalenesulfonate                                                                            2%                                                low viscosity methyl cellulose                                                                              2%                                                diatomaceous earth           46%                                               ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.

EXAMPLE 12

    ______________________________________                                         Granule                                                                        ______________________________________                                         Wettable Powder of Example 11                                                                         5%                                                      attapulgite granules  95%                                                      ______________________________________                                          (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                        

A slurry of wettable powder containing ≈25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.

EXAMPLE 13

    ______________________________________                                         Extruded Pellet                                                                ______________________________________                                         N--[(4,6-dimetylpyrimidin-2-yl)aminocarbonyl]-2-[(1-                                                       25%                                                methylethyl)sulfonyl]benzenesulfonamide                                        anhydrous sodium sulfate    10%                                                crude calcium ligninsulfonate                                                                               5%                                                sodium alkylnaphthalenesulfonate                                                                            1%                                                calcium/magnesium bentonite 59%                                                ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

EXAMPLE 14

    ______________________________________                                         Oil Suspension                                                                 ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-                                                        25%                                                 (popylsulfonyl)benzenesulfonamide                                              polyoxyethylene sorbitol hexaoleate                                                                        5%                                                 highly aliphatic hydrocarbon oil                                                                          70%                                                 ______________________________________                                    

The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

EXAMPLE 15

    ______________________________________                                         Wettable Powder                                                                ______________________________________                                         N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-                                                     20%                                               (propylsulfonyl)benzenesulfonamide                                             sodium alkylnaphthalenesulfonate                                                                            4%                                                sodium ligninsulfonate       4%                                                low viscosity methyl cellulose                                                                              3%                                                attapulgite                  69%                                               ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.

EXAMPLE 16

    ______________________________________                                         Low Stength Granule                                                            ______________________________________                                         N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbon-                                                     1%                                                yl]-2-(propylsulfonyl)benzenesulfonamide                                       N,N--dimethylformamide       9%                                                attapulgite granules         90%                                               (U.S.S. 20-40 sieve)                                                           ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.

EXAMPLE 17

    ______________________________________                                         Aqueous Suspension                                                             ______________________________________                                         N--[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-                                                     40%                                                (propylsulfonyl)benzenesulfonamide                                             polyacrylic acid thickener  0.3%                                               dodecylphenol polyethylene glycol ether                                                                    0.5%                                               disodium phosphate           1%                                                monosodium phosphate        0.5%                                               polyvinyl alcohol           1.0%                                               water                       56.7%                                              ______________________________________                                    

The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.

EXAMPLE 18

    ______________________________________                                         Solution                                                                       ______________________________________                                         N--[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbon-                                                     5%                                                yl]-2-[(1-methylethyl)sulfonyl]benzene-                                        sulfonamide, sodium sa1t                                                       water                        95%                                               ______________________________________                                    

The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.

EXAMPLE 19

    ______________________________________                                         Low Strength Granule                                                           ______________________________________                                         N--[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                        0.1%                                             2-(propylsulfonyl)benzenesulfonam1de                                           attapulgite granules         99.9%                                             (U.S.S. 20-40 mesh)                                                            ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.

EXAMPLE 20

    ______________________________________                                         Granule                                                                        ______________________________________                                         N--[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-                                                          80%                                                (propy1sulfonyl)benzenesulfonamide                                             wetting agent                1%                                                crude liginsulfonate salt (containing                                                                      10%                                                5-20% of the natural sugars)                                                   attapulgite clay             9%                                                ______________________________________                                    

The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.

EXAMPLE 21

    ______________________________________                                         High Strength Concentrate                                                      ______________________________________                                         N--[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-                                                        99%                                              2-(propylsulfonyl)benzenesulfonamide                                           silica aerogel               0.5%                                              synthetic amorphous silica   0.5%                                              ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.

EXAMPLE 22

    ______________________________________                                         Wettable Powder                                                                ______________________________________                                         N--[ (4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-                                                    90%                                                [(1-methylethyl)sulfonyl]benzenesulfonamide                                    dioctyl sodium sulfosuccinate                                                                             0.1%                                                synthetic fine silica      9.9%                                                ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.

EXAMPLE 23

    ______________________________________                                         Wettable Powder                                                                ______________________________________                                         N--[(4-dimethylamino-6-methoxy-l,3,5-triazin-2-yl)-                                                       40%                                                 aminocarbonyl]-2-(propylsulfonyl)benzene-                                      sulfonamide                                                                    sodium ligninsulfonate     20%                                                 montmorillonite clay       40%                                                 ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.

EXAMPLE 24

    ______________________________________                                         Oil Suspension                                                                 ______________________________________                                         N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-                                                    35%                                                [(1-methylethyl)sulfonyl]benzenesulfonamide                                    blend of polyalcohol carboxylic                                                                             6%                                                esters and oil soluble petroleum                                               sulfonates                                                                     xylene                      59%                                                ______________________________________                                    

The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.

The compounds of Formula I can be formulated using the procedures of Examples 10-24.

UTILITY

The compounds of the present invention are active herbicides. They have utility for broad-spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, MX missile sites, parking lots, drive-in theaters, around billboards, highway and railroad structures. In addition, the subject compounds distinguish themselves in being highly useful for the selective pre- or post-emergence weed control in a wide range of crops, such as soybeans, dry beans, green beans, alfalfa, tobacco, corn, cotton, wheat, barley, cucumbers, tomatoes, flax and potatoes. By properly selecting rate and time of application, compounds of this invention may be used also to modify plant growth beneficially.

The rates of application for the compounds of the invention are determined by a number of factors, including their use as selective or general herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.01 to 10 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for selective weed control or for situations where only short-term persistence is required.

The compounds of this invention may be used in combination with other commercial herbicides. They are particularly useful in combination with the following herbicides.

    ______________________________________                                         Common                                                                         Name     Chemical Name                                                         ______________________________________                                         acifluorfen                                                                             5-[2-chloro-4-(trifluoromethyl)phenoxy]-                                       2-nitrobenzoic acid                                                   alachlor 2-chloro-2',6'-diethyl-N--(methoxymethyl)-                                     acetanilide                                                           amitrole 3-amino- .sub.-s-triazole                                             atrazine 2-chloro-4-(ethylamino)-6-(isopropyl-                                          amino)- .sub.-s-triazine                                              barban   4-chloro-2-butynyl  .sub.--m-chlorocarbanilate                        bentazon 3-isopropyl-1H--2,1,3-benzothiadiazin-                                         4(3H)--one-2,2-dioxide                                                benzoylprop                                                                             N--benzoyl-N--(3,4-dichlorophenyl)-DL-                                         alaine                                                                bromacil 5-bromo-3-sec-butyl-6-methyluracil                                    bromoxynil                                                                              3,5-dibromo-4-hydroxybenzonitrile                                     butylate S--ethyl-diisobutylthiocarbamate                                      Chloramben                                                                              3-amino-2,5-dichlorobenzoic acid                                      chlortoluron                                                                            N'--(3-Chloro-4-methylphenyl-N',N'--                                           dimethylurea                                                          cyanazine                                                                               2-[[4-chloro-6-(ethylamino)- .sub.-s-triazin-                                  2-yl]amino]-2-methylpropionitrile                                     diallate S--(2,3-dichloroallyl)diisopropylthio-                                         carbamate                                                             dicamba  3,6-dichloro- -o-anisic acid                                          dichloroprop                                                                            2-(2,4-dichlorophenoxy)propionic acid                                 diclofop 2-[4-(2,4-dichlorophenoxy)phenoxy]-                                            propanoic acid                                                        difenzoquat                                                                             1,2-dimethyl-3,5-diphenyl-1H--pyrazolium                              dinoseb  2-sec-butyl-4,6-dinitrophenol                                         diuron   3-(3,4-dichlorophenyl)-1,1-dimethylurea                               EPTC     S--ethyl-dipropylthiocarbamate                                        flamprop N--benzoyl-N--(3-chloro-4-fluorophenyl)-DL-                                    alanine                                                               fluazifop-                                                                              butyl 2-[4-[5-(trifluoromethyl)-2-pyri-                               butyl    dinyloxy]phenoxy]propanoate                                           fluchloralin                                                                            N--(2-chloroethyl)-2,6-dinitro-N--propyl-4-                                    trifluoromethyl)aniline                                               fluometuron                                                                             1,1-dimethyl-3-(α,α,α-trifluoro- .sub.--m-tolyl              )-                                                                             urea                                                                  fomesafen                                                                               5-(2-chloro-4-trifluoromethylphenoxy)-                                         N--methylsulfonyl-2-nitrobenzamide                                    fosamine ethyl hydrogen (aminocarbonyl)phosphonate                             glyphosate                                                                              N--(phosphonomethyl)glycine                                           hexazinone                                                                              3-cyclohexyl-6-(dimethylamino)-1-methyl-                                       1,3,5-triazine-2,4(1H,3H)--dione                                      ioxynil  4-hydroxy-3,5-diiodobenzonitrile                                      isoproturon                                                                             N--(4-isopropylphenyl)-N',N'--dimethylurea                            lenacil  3-cyclohexyl-6,7-dihydro-1H--cyclopenta-                                       pyrimidine-2,4(3H,5H)--dione                                          linuron  3-(3,4-dichlorophenyl)-1-methoxy-1-                                            methylurea                                                            MCPA     [(4-chloro- -o-tolyl)oxy]acetic acid                                  MCPB     4-[(4-chloro- -o-tolyl)oxy]propionic acid                             mefluidide                                                                              N--[2,4-dimethyl-5-[[(trifluoromethyl)-                                        sulfonyl]amino]phenyl]acetamide                                       methabenz-                                                                              1,3-dimethyl-3-(2-benzothiazolyl)urea                                 thiazuron                                                                               N'--(3-chloro-4-methoxyphenyl)N,N--                                   methoxuron                                                                              dimethylurea                                                          metolachlor                                                                             2-chloro-N--(2-ethyl-6-methylphenyl)-N--                                       (2-methoxy-1-methylethyl)acetamide                                    metibuzin                                                                               4-amino-6-tert-butyl-3-(methylthio)-as-                                        triazin-5(4H)--one                                                    MSMA     monosodium methanearsonate                                            neburon  1-butyl-3-(3,4-dichlorophenyl)-1-methyl-                                       urea                                                                  oryzalin 3,4-dinitro-N,N--dipropylsulfanilamide                                paraquat 1,1'-dimethyl-4,4'-bipyridinium ion                                   pendimethalin                                                                           N--(1-ethylpropyl)-3,4-dimethyl-2,6-                                           dinitrobenzeneamine                                                   profluralin                                                                             N--(cyclopropylmethyl)-α,α,α-trifluoro-                      2,6-dinitro-N'propyl- -p-toluidine                                    propanil 3',4'-dichloropropionalide                                            sethoxydim                                                                              2-[1-(ethoxyimino)butyl]-5-[2-(ethyl-                                          thio)propyl]3-hydroxy-2-cyclohexene-                                           1-one                                                                 siduron  1-(2-methylcyclohexyl)-3-phenylurea                                   supriox  2-[1-(2,5-dimethylphenyl)ethylsulfonyl]-                                       pyridine-N--oxide                                                     terbacil 3-tert-butyl-5-chloro-6-methyluracil                                  triallate                                                                               S--(2,3,3-trichloroallyl)diisopropylthio-                                      carbamate                                                             trifluralin                                                                             α,α,α-trifluoro-2,6-dinitro-N,N--dipropyl-                    -p-toluidine                                                         2,4-D    (2,4-dichlorophenoxy)acetic acid                                      2,4-DB   4-(2,4-dichlorophenoxy)butyric acid                                            3,4-diaryl-4-cyanobutyrates                                                    4-(6-chloroquinoxalinyl-2-oxy)phenoxy-                                         propionate C.sub.1 -C.sub.5 alkyl esters, such                                 as methyl ester, butyl ester, ethyl                                            ester, pentyl ester                                                            ethoxyethoxyethyl 4-(6-chloroquinoxalin-                                       yl-2-oxy)phenoxypropionate                                                     propargyl 2-[4-(3,5-dichloropyridin-2-                                         yloxy)phenoxy]propanoate                                                       methyl 2-[4-(3-chloro-5-trifluoromethyl-                                       pyridin-2-yloxy)phenoxy]propanoate                                    oxyfluorfen                                                                             2-ch1oro-1-(3-ethoxy-4-nitrophenoxy)-4-                                        (trifluoromethyl)benzene                                              norflurazon                                                                             4-chloro-5-(methylamino)-2-[(3-(tri-                                           fluoro)phenyl]-3(2H)--pyridazinone                                    vernolate                                                                               S--propyl dipropylthiocarbamate                                                ethyl 5-[2-chloro-4-(trifluoromethyl)-                                         phenoxy]-2-nitrobenzoic acid                                          ______________________________________                                    

The activity of these compounds was discovered in a number of greenhouse and field tests. The tests are described and the data resulting from them are shown in the following tables.

0=no effect

10=maximum effect

C=chlorosis or necrosis

D=defoliation

E=emergence inhibition

G=growth retardation

H=formative effects

U=unusual pigmentation

X=axillary stimulation

5F=earlier flowering

6Y=abscised buds or flowers.

TEST A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), cassia (Cassia tora), morningglory (Ipomoea spp.), cocklebur (Xanthium spp.), sorghum, corn, soybean, rice, wheat and nutsedge tubers (Cyperus rotundus) were planted in a growth medium and treated pre-emergence with a non-phytotoxic solvent solution of the compounds of Table A. At the same time, cotton having five leaves (including cotyledonary ones), bush beans with the third trifoliate leaf expanding, crabgrass, barnyardgrass and wild oats with two leaves, cassia with three leaves (including cotyledonary ones), morningglory and cocklebur with four leaves (including the cotyledonary ones), sorghum and corn with four leaves, soybean with two cotyledonary leaves, rice with three leaves, wheat with one leaf, and nutsedge with three-five leaves were sprayed with a non-phytotoxic solvent solution of the compounds of Table A. Other containers of the above mentioned weeds and crops were treated pre- or post-emergence with the same non-phytotoxic solvent so as to provide a solvent control. A set of untreated control plants was also included for comparison. Pre-emergence and post-emergence treated plants and controls were maintained in a greenhouse for sixteen days, then all treated plants were compared with their respective controls and rated visually for response to treatment. The data in Table A shows that the compounds of this invention are very effective as herbicides and have utility for selective post-emergence weed control in wheat. ##STR112##

                                      TABLE A                                      __________________________________________________________________________             Compound No.                                                                   1     2      3   4     5    6                                          kg/ha   0.1   0.1    0.1 0.1   0.1  0.1                                        __________________________________________________________________________     POST-EMERGENCE                                                                 Bushbean                                                                               2C,5G,6Y                                                                             5C,8G,6Y                                                                              9C  3C,6Y 9C   9C                                         Cotton  3C,3H,6G                                                                             4C,7G  5C,9G                                                                              3C,3H 6C,8G                                                                               6C,9G                                      Morningglory                                                                           2C,5G,5F                                                                             l0C    1C,2H                                                                              2C,4G,5F                                                                             6C,9G                                                                               10C                                        Cocklebur                                                                              2C,5G 9C     9C  2C,2H 5C,9G                                                                               9C                                         Cassia  3C    5C,8G  4C,8G                                                                              1C    2C,5G                                                                               5C,8G                                      Nutsedge                                                                               2G    5G     7G  0     1C   5G                                         Crabgrass                                                                              2G    2G     2G  1C,2G 1C,5G                                                                               2C,8G                                      Barnyardgrass                                                                          2C,5H 9C     8H  9C    5C,9H                                                                               2C,9H                                      Wild Oats                                                                              2C,6G 2C,5G  1C  2C,3G 2C   1C,2G                                      Wheat   1C,2G 2C,3G  1C  1C    1C,2G                                                                               1G                                         Corn    2C    1C,3G  1C,5H                                                                              1C,5H 4C,9H                                                                               9C                                         Soybean 2C,6G 5C,9G  2C,8G                                                                              2C    5C,9G                                                                               6C,9G                                      Rice    --    --     --  --    --   --                                         Sorghum 3C,9H 3C,9G  2C,9G                                                                              1C,9G 2C,9G                                                                               4C,9G                                      PRE-EMERGENCE                                                                  Morningglory                                                                           8G    9G     9G  7G    9C,9G                                                                               9C,9G                                      Cocklebur                                                                              5H    9H     9H  4G    9H   9H                                         Cassia  1C    8G     8G  1C    2C,9G                                                                               2C,9G                                      Nutsedge                                                                               0     10E    10E 1C,5G 9G   10E                                        Crabgrass                                                                              2G    5G     1C,8G                                                                              2C    2C,8G                                                                               2C,8G                                      Barnyardgrass                                                                          1C,3G 9H     9H  2C,4G 2C,9H                                                                               3C,9H                                      Wild Oats                                                                              1C,2G 2C,8H  7G  2C    2C,7G                                                                               1C,2G                                      Wheat   1C    1C,5G  4G  0     1C,5G                                                                               5G                                         Corn    3G    1C,7G  1C,9H                                                                              1C,6G 1U,9G                                                                               1U,9G                                      Soybean 0     8H     7H  0     8H   8H                                         Rice    2C,6H 9H     10E 9H    9H   9H                                         Sorghum 1C,8G 5C,9H  2C,9H                                                                              1C,9G 5C,9H                                                                               3C,9H                                      __________________________________________________________________________             Compound No.                                                                   7     8   9   10    11    12                                           kg/ha   0.4   0.4 0.4 0.4   0.4   0.4                                          __________________________________________________________________________     POST-EMERGENCE                                                                 Bushbean                                                                               9C    9C  9C  9C    9C    5C,9G                                        Cotton  2U,6C,9G                                                                             9C  9C  2U,5C,9G                                                                             9C    9C                                           Morningglory                                                                           10C   10C 10C 9C    10C   10C                                          Cocklebur                                                                              9C    10C 9C  9C    9C    10C                                          Cassia  4C,8G 9C  9C  5C,8G 9C    9C                                           Nutsedge                                                                               1C,8G 1C,9G                                                                              5C,9G                                                                              4G    6G    1C,6G                                        Crabgrass                                                                              3C,9G 5C,9G                                                                              7C,9G                                                                              2C,8G 6C,9G 4C,9G                                        Barnyardgrass                                                                          9C    9C  9C  2C,9H 9C    9C                                           Wild Oats                                                                              9C    9C  5C,9H                                                                              5C,8G 6C,9G 3C,7H                                        Wheat   3C,9G 3C,9G                                                                              3C,9G                                                                              1C,7G,5X                                                                             2C,9G,5X                                                                             1C,6G,5X                                     Corn    2U,9H 7U,9G                                                                              3U,9H                                                                              2U,9G 8U,9G 6U,9C                                        Soybean 9C    9C  9C  2C,8G,5X                                                                             9C    9C                                           Rice    9C    9C  8C  5C,9G 7C,9G 9C                                           Sorghum 9C    10C 9C  9C    9C    4U,9C                                        PRE-EMERGENCE                                                                  Morningglory                                                                           9C    9H  9H   9G   9H    9H                                           Cocklebur                                                                              9H    10E 9H  9H    9H    9H                                           Cassia  2C,9G 2C,9G                                                                              2C,9G                                                                              6C,9G 2C,9G 1C,9G                                        Nutsedge                                                                               10E   10E 10E 4G    2C,8G 8G                                           Crabgrass                                                                              1C,5G 5C,9G                                                                              5C,9H                                                                              2G    4C,9G 2C,8G                                        Barnyardgrass                                                                          3C,9H 5C,9H                                                                              5C,9H                                                                              4C,9H 5C,9H 4C,9H                                        Wild Oats                                                                              4C,9H 5C,9H                                                                              5C,9H                                                                              2C,8G 5C,9H 5C,9H                                        Wheat   1C,9G 2C,9G                                                                              3C,9H                                                                              1C,8G 3C,9G 1C,9G                                        Corn    2C,9G 9H  9G  9H    10E   10E                                          Soybean 9H    9H  9H  1C,2G 9H    2C,9H                                        Rice    10E   10E 10E 10E   10E   10E                                          Sorghum 3C,9H 6C,9H                                                                              10H 3C,9H 10H   6C,9H                                        __________________________________________________________________________

TEST B

Two plastic bulb pans were filled with fertilized and limed Fallsington silt loam soil. One pan was planted with corn, sorghum, Kentucky bluegrass and several grassy weeds. The other pan was planted with cotton, soybeans, purple nutsedge (Cyperus rotundus), and several broadleaf weeds. The following grassy and broadleaf weeds were planted: crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense), dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii), cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthium pensylvanicum), pigweed (Amaranthus retroflexus), morningglory (Ipomoea hederacea), cassia (Cassia tora), teaweed (Sida spinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). A 12.5 cm diameter plastic pot was also filled with prepared soil and planted with rice and wheat. Another 12.5 cm pot was planted with sugarbeets. The above four containers were treated pre-emergence with several test compounds within the scope of the invention.

Twenty-eight days after treatment, the plants were evaluated and visually rated for response to the chemical treatments utilizing the rating system described previously. The data are summarized in Table B. It will be readily seen that certain compounds are useful as pre-emergence treatments for weed control in crops such as soybeans, wheat, corn and cotton.

                                      TABLE B                                      __________________________________________________________________________     PRE-EMERGENCE ON FALLSINGTON SILT LOAM                                         __________________________________________________________________________             Compound No.                                                                   7       8       2               9                                      kg/ha   0.03                                                                               0.12                                                                               0.03                                                                               0.12                                                                               0.03                                                                               0.06                                                                               0.12                                                                               0.25                                                                               0.03                                                                               0.06                                                                               0.12                                                                               0.25                       __________________________________________________________________________     Crabgrass                                                                              0   2G  5G  6G  0   6G  3G  5G  5G  7G  6G  8G                         Barnyardgrass                                                                          5G  7G,3H                                                                              9G,8C                                                                              9G,9C                                                                              6G,3C                                                                              8G,3H                                                                              8G,4C                                                                              9G,9C                                                                              8G,3H                                                                              9G,5H                                                                              9G,9C                                                                              10C                        Sorghum 9G,5H                                                                              9G,9C                                                                              10C 10C 8G,5H                                                                              9G,9C                                                                              10C 10C 9C,9C                                                                              10C 10C 10C                        Wild Oats                                                                              7G,3H                                                                              7G,4C                                                                              7G,6C                                                                              7G,6C                                                                              4G  4G,3C                                                                              7G,4C                                                                              6G,5C                                                                              5G,3C                                                                              3G  7G,3C                                                                              6G,3C                      Johnsongrass                                                                           6G,3H                                                                              8G,3H                                                                              8G,4C                                                                              7G,4C                                                                              6G,3H                                                                              8G,5H                                                                              7G,3H                                                                              9G,7C                                                                              7G,3H                                                                              8G,3H                                                                              8G,3C                                                                              9G,9C                      Dallisgrass                                                                            0   6G  8G  9G,8C                                                                              6G  --  7G  --  7G  --  8G  --                         Giant Foxtail                                                                          0   6G,3H                                                                              7G,4C                                                                              7G,4C                                                                              5G  6G,3C                                                                              7G,3C                                                                              7G,3C                                                                              6G,3C                                                                              7G,5H                                                                              8G,6C                                                                              9G,8C                      Ky. Bluegrass                                                                          5G  7G  9G,9C                                                                              10C 8G,5C                                                                              6G,3C                                                                              8G,8C                                                                              8G,5C                                                                              8G,7C                                                                              8G,5C                                                                              8G,8C                                                                              8G,8C                      Cheatgrass                                                                             7G,5E                                                                              9G,9C                                                                              10C 10C 7G,3C                                                                              8G,8C                                                                              8G,3C                                                                              10E 8G,4C                                                                              10E 8G,6C                                                                              10E                        Sugarbeets                                                                             6G,7C                                                                              8G,8C                                                                              8G,8C                                                                              8G,9C                                                                              5G  7G,5H                                                                              6G,3C                                                                              8G,8C                                                                              7G,7C                                                                              6G,3H                                                                              7G,7C                                                                              8G,8C                      Corn    2G  4G,2C                                                                              6G,3H                                                                              8G,5H                                                                              0   5G  2H  5G,3H                                                                              0   5G,2C                                                                              4G,3H                                                                              6G,3C                      Mustard 9G,9C                                                                              9G,9C                                                                              9G,9C                                                                              10C 9G,9C                                                                              9G,8C                                                                              10C 10C 9G,9C                                                                              10C 10C 10C                        Cocklebur                                                                              3G  5G  7G  8G  6G  5G,3H                                                                              6G  6G,5H                                                                              6G  5G,3H                                                                              7G  7G,3H                      Pigweed 7G  7G  10C 10C 3G  6G  10C 8G,8C                                                                              5G  4G  9G,9C                                                                              10C                        Nutsedge                                                                               0   3G  8G  7G  5G  6G  6G  7G  10E 7G  8G  10E                        Cotton  0   4G,2H                                                                              7G,5H                                                                              7G,5H                                                                              0   4G  5G,5H                                                                              6G,5H                                                                              4G,3H                                                                              6G  7G,5H                                                                              8G,5H                      Morninglory                                                                            7G,5H                                                                              8G,5H                                                                              7G,5H                                                                              8G,5H                                                                              4G  4G,2H                                                                              8G  8G,5H                                                                              6G  7G,5H                                                                              7G  10C                        Cessia  5G  5G  7G,4C                                                                              10E 0   2G,2C                                                                              5G,3C                                                                              8G,3H                                                                              8G,5C                                                                              6G,3C                                                                              8G,5C                                                                              9G,6C                      Teaweed 0   8G,3C                                                                              5G,3C                                                                              6G,3C                                                                              2G  0   3G  5G,3H                                                                              5G,2C                                                                              3G  5G,2C                                                                              7G                         Velvetleaf                                                                             5G,3H                                                                              7G,3H                                                                              8G,5C                                                                              9G,9C                                                                              3H  3H  6G,5H                                                                              6G,5H                                                                              8G,5H                                                                              7G,5H                                                                              9G,9C                                                                              8G,7C                      Jimsonweed                                                                             4G  5G  6G,3C                                                                              7G,5C                                                                              4G,3C                                                                              7G  7G,5C                                                                              7G,3C                                                                              3G  0   4G  4G                         Soybean 0   3G  4G,3H                                                                              6G,5H                                                                              0   4G  4G,2C                                                                              6G,3H                                                                              0   0   4G  5G,3H                      Rice    7G  10E 9G,9C                                                                              10C 5G  6G,3H                                                                              7G,3C                                                                              7G,5H                                                                              10E 8G,8C                                                                              10E 10E                        Wheat   3G  5G  5G  6G  2G  2G  5G  3G  0   2G  3G  5G                         __________________________________________________________________________             Compound No.                                                                   3               11              10      5                              kg/ha   0.03                                                                               0.06                                                                               0.12                                                                               0.25                                                                                0.03                                                                              0.06                                                                               0.12                                                                               0.25                                                                               0.03                                                                               0.12                                                                               0.03                                                                               0.12                       __________________________________________________________________________     Crabgrass                                                                              3G  0   6G  5G  2G  4G  6G  7G  0   2G  0   5G                         Barnyardgrass                                                                          5G,2C                                                                              7G,3H                                                                              8G,3C                                                                              8G,3H                                                                              4G  6G  8G,7C                                                                              8G,6C                                                                              3G  3G  4G  7G,3C                      Sorghum 9C,9C                                                                              10C 9G,9C                                                                              10C 9C,9C                                                                              10C 10E 10C 3G  8G,5H                                                                              9G,8C                                                                              10C                        Wild Oats                                                                              4G  0   7G,3C                                                                              5G  6G,2H                                                                              4G,3C                                                                              7G,3H                                                                              6G,4C                                                                              0   6G,3H                                                                              3G  6G                         Johnsongrass                                                                           7G,3H                                                                              7G,5H                                                                              8G,5C                                                                              8G,5H                                                                              8G,5C                                                                              9C,7C                                                                              8G  9G,9C                                                                              0   6G,3H                                                                              7G,3H                                                                              8G                         Dallisgrass                                                                            6G  0   8G  6G,3H                                                                              5G  --  5G  --  0   5G  0   4G                         Giant Foxtail                                                                          8G,4C                                                                              8G,5H                                                                              9G,9C                                                                              9G,5H                                                                              3G,2C                                                                              5G  6G,3C                                                                              6G,2C                                                                              0   0   4G  6G,3C                      Ky. Bluegrass                                                                          7G,5C                                                                              7G,8C                                                                              8G,9C                                                                              9G,9C                                                                              6G,2C                                                                              7G,4C                                                                              7G,3C                                                                              8G,8C                                                                              0   3G  6G  7G,3C                      Cheatgrass                                                                             8G,5C                                                                              8G,5H                                                                              8G,8C                                                                              8G,9C                                                                              7G  10C 8G,3C                                                                              7G,3C                                                                              6G  6G,5E                                                                              3G  7G                         Sugarbeets                                                                             6G,3C                                                                              7G,5H                                                                              8G,8C                                                                              9G,9C                                                                              8G,8C                                                                              10C 9G,9C                                                                              10C 0   7G,5H                                                                              10C 8G,7C                      Corn    2G  0   6G,3H                                                                              5G,3H                                                                              9G,3C                                                                              6G,5H                                                                              9G,5C                                                                              10C 0   5G,3C                                                                              7G,3H                                                                              8G                         Mustard 9G,8C                                                                              9G,9C                                                                              10C 10C 10C 10C 10C 10C 4G  8G,8C                                                                              8G,8C                                                                              10C                        Cocklebur                                                                              7G  7G,3H                                                                              7G  7G,5H                                                                              8G,5H                                                                              7G,5H                                                                              8G,5H                                                                              8G,5H                                                                              --  3G  7G,3H                                                                              8G,5H                      Pigweed 6G,5C                                                                              10C 10C 10C 10C 8G,8C                                                                              8G,9C                                                                              10C 0   5G  9G,9C                                                                              10E                        Nutsedge                                                                               9G  7G  10E 8G  6G  0   6G  5G  0   0   5G  6G                         Cotton  0   3G  4H  6G,5H                                                                              8G,5H                                                                              8G,5H                                                                              8G,5H                                                                              9G,5H                                                                              0   5H  6G,5H                                                                              8G,5H                      Morninglory                                                                            7G  3G  7G  6G  8G  8G,5H                                                                              8G  9G,8C                                                                              0   5H  7G,5H                                                                              8G,3C                      Cessia  0   5G  8G,3C                                                                              8G  9G,5C                                                                              7G,3H                                                                              9G,8C                                                                              9G,7C                                                                              0   0   7G,5C                                                                              9G                         Teaweed 3G  7G  6G,3C                                                                              8G  7G,2C                                                                              5G,5H                                                                              8G,2C                                                                              7G,5H                                                                              0   0   0   4G,3H                      Velvetleaf                                                                             7G,5H                                                                              4G,5H                                                                              8G,5H                                                                              8G,5E                                                                              8G,7C                                                                              7G,5H                                                                              8G,7C                                                                              8G,6C                                                                              0   4G  6G,5H                                                                              8G,5C                      Jimsonweed                                                                             4G  0   5G  0   5G,3C                                                                              8G  7G,5C                                                                              8G  0   0   4G,3C                                                                              7G,4C                      Soybean 0   1C  3G,2H                                                                              5G,2C                                                                              0   0   3G,2H                                                                              5G,5H                                                                              0   0   4G,3H                                                                              8G,5H                      Rice    8G,9C                                                                              10E 8G,9C                                                                              10C 8G,8C                                                                              7G,3H                                                                              10E 10E 2G  6G,3C                                                                              5G  7G,8C                      Wheat   2G  2G  2G  3G  4G  0   5G  5G  0   4G  0   5G                         __________________________________________________________________________                                     Compound No.                                                                   12              6                                                      kg/ha   0.03                                                                               0.06                                                                               0.12                                                                               0.25                                                                               0.03                                                                               0.12                       __________________________________________________________________________                             Crabgrass                                                                              0   3G  5G  7G  2G  7G                                                 Barnyardgrass                                                                          6G  5G  8G,4C                                                                              8G,3C                                                                              5G  7G,2C                                              Sorghum 9C,9C                                                                              9G,9C                                                                              10C 10C 9G,8C                                                                              10C                                                Wild Oats                                                                              9G,9C                                                                              9G,4C                                                                              6G,3H                                                                              6G,3H                                                                              2G  6G,2H                                              Johnsongrass                                                                           7G,3H                                                                              7G,3H                                                                              8G,3H                                                                              8G,5H                                                                              7G,3H                                                                              8G,3H                                              Dallisgrass                                                                            0   --  0   --  0   4G                                                 Giant Foxtail                                                                          0   0   4G  5G,3C                                                                              0   4G                                                 Ky. Bluegrass                                                                          5G  5G  7G,3C                                                                              7G,5C                                                                              5G  6G                                                 Cheatgrass                                                                             0   5G,5C                                                                              6G,3C                                                                              4G,3C                                                                              3G  7G,3C                                              Sugarbeets                                                                             8G,7C                                                                              10C 8G,8C                                                                              10C 10C 8G,8C                                              Corn    7G,3H                                                                              7G,5H                                                                              7G,3H                                                                              7G,5H                                                                              7G,5H                                                                              8G,4C                                              Mustard 10C 9G,9C                                                                              10C 10C 6G  7G,2C                                              Cocklebur                                                                              7G,3H                                                                              6G,3H                                                                              8G,5H                                                                              8G,5H                                                                              6G,3H                                                                              7G,5H                                              Pigweed 9G,9C                                                                              9G,9C                                                                              10E 9G,9C                                                                              8G,7C                                                                              10C                                                Nutsedge                                                                               6G  3G  6G  6G  6G  6G                                                 Cotton  7G,5H                                                                              8G,5H                                                                              8G,5H                                                                              9G,5H                                                                              7G,5H                                                                              8G,5H                                              Morningglory                                                                           8G  8G,7C                                                                              9G,8C                                                                              9G,3C                                                                              6G,5H                                                                              8G                                                 Cassia  7G,3C                                                                              7G,3H                                                                              8G,5C                                                                              8G,7C                                                                              7G,3C                                                                              8G,5C                                              Teaweed 5G,5H                                                                              3H  6G,5H                                                                              8G,5H                                                                              0   4G,3H                                              Velvetleaf                                                                             6G,5H                                                                              6G,5H                                                                              8G,5C                                                                              9G,9C                                                                              4G,3H                                                                              7G,5H                                              Jimsonweed                                                                             2G  5G  5G  7G  0   7G,5C                                              Soybean 0   2G  2G  2G  0   6G,3H                                              Rice    5G,3C                                                                              7G,3H                                                                              9G,9C                                                                              9G,9E                                                                              6G,3C                                                                              7G,8C                                              Wheat   0   3G  4G  4G  0   3G,2C                      __________________________________________________________________________

TEST C

The high herbicidal activity and selective properties of several of the compounds from within the scope of the invention is evident from the results obtained in this test. The experiment concerned pre-emergence applications on soil. The containers used were 25 cm diameter plastic pots filled with Fallsington silt loam. One set of pots was planted to weeds, the seeds of which were uniformly mixed with th top 1.2 cm layer of soil. The species selected were: johnsongrass (Sorghum halepense), barnyardgrass (Echinochloa crusgalli), crabgrass (Digitaria sanguinalis), giant foxtail (Setaria faberii), velvetleaf (Abutilon theophrasti), jimsonweed (Datura stramonium), mustard (Brassica arvensis), and pigweed (Amaranthus retroflexus). Another set of pots was planted to the following crops with from one to four species per pot: corn (planting dept 3.7 cm), cotton, soybeans, sunflower, Clinton oats, wheat, Black Velentine beans, rice, sorghum, peas, flax, and peanuts (all at 2.5 cm depth), cucumbers, cabbage, alfalfa, safflower, sugarbeets, tomato, spinach, barley, and Kentucky bluegrass (all at 1.2 cm depth). Immediately after planting, the test chemicals were applied to the soil surfaces dissolved in a non-phytotoxic solvent. In the case of tobacco, a solution containing the test chemical was drenched on the surface of the soil surrounding newly transplanted tobacco seedlings. One pot from the weed phase and one of each of the crop species were left untreated for the purpose of comparison. The treated and untreated pots were promptly watered with approximately 4 mm of simulated rainfall and then held in a greenhouse for several weeks. Visual weed and crop response ratings were made 28 days after treatment utilizing the rating system as described above. The data are given in Table C. The data clearly indicate that compounds from within the scope of the present invention have utility for selective pre-emergence weed control in crops such as soybeans, alfalfa, wheat, oats, barley, cucumber, and tomato. In the case of at least one compound, weed control is obtained by applying the chemical in the form of a drench on the soil around newly-transplanted tobacco seedlings.

                                      TABLE C                                      __________________________________________________________________________     PRE-EMERGENCE ON FALLSINGT0N SILT LOAM                                                Compound No. 3  Compound No. 11 Compound No. 12                         kg/ha  1/64                                                                               1/32                                                                               1/l6                                                                               1/8 1/l28                                                                              1/64                                                                               1/32                                                                               1/l6                                                                               1/l28                                                                              1/64                                                                              1/32                                                                               1/l6                         __________________________________________________________________________     Corn               7G,5H           8G,8C          8G,8C                        Cotton             7G,5H           7G,5H          8G,5H                        Soybean            7G,5H           0              0                            Peanut             7G,5H           --             --                           Sunflower          8G,5H           9G,8C          9G,8C                        Oats               4G              6G,2C          5G,2C                        Wheat              2G              5G             4G                           Sorghum            l0E             9G,9C          8G,8C                        Sugarbeet          8G,7C           9G,9C          9G,9C                        Pea                9G,9C           l0E            10E                          Flax               9G,9C           7G,5E          8G,8C                        Alfalfa            8G,8C           7G,3C          4G                           Bean               7G,5H           8G,5H          5G,3H                        Spinach            9G,8C           8G,8C          8G,9C                        Cabbage            9G,9C           8G,7C          8G,6C                        Tomato             4G              7G,5H          2G                           Rice               10E             7G,7C          9G,8C                        Safflower          8G,6C           8G,3C          8G,3C                        Cucumber           9G,5H           9G             5G                           Ky. Bluegrass      8G,9C           7G             6G                           Barley             8G,6C           3G             3G                           Tobacco            0               --             --                           Broadleaves                                                                           2G,3C                                                                              4G,4C                                                                              5G,4C   5G,3C                                                                              7G,7C                                                                              8G,7C   3G  2G 5G,3C                            Grasses                                                                               5G,2C                                                                              6G,3C                                                                              7G,5C   2G  3G  4G      3G  0  3G                               __________________________________________________________________________

TEST D

Twenty-five cm diameter plastic pots filled with Fallsington silt loam were planted with soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata), Cassia (Cassia tora), morningglory (Ipomoea hederacea), jimsonweed (Datura stramonium), cocklebur (Xanthium pensylvanicum), crabgrass (Digitaria spp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloa crusgalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua). In the case of compound No. 13, the following additional species were included: sunflower, mustard, sugarbeets and bushbean. Approximately 21/2 weeks after planting, the young plants and the soil around them were sprayed overall with the test chemicals dissolved in a non-phytotoxic solvent. Two weeks after treatment, all species were compared to untreated controls and visually rated for response to treatment. The rating system was as described previously for Test A. The data are pesented in Table D. Several of the compounds tested by this procedure are useful for the post-emergence control of weeds in wheat, corn and soybeans.

                                      TABLE D                                      __________________________________________________________________________     Over-the-Top Soil/Foliage Treatment                                            __________________________________________________________________________             Compound No. 7     Compound No. 8                                                                               Compound No. 9                        kg/ha   0.016                                                                              0.031                                                                               0.063                                                                               0.125                                                                               0.016                                                                              0.031                                                                               0.125                                                                               0.016                                                                               0.031                                                                               0.063                       __________________________________________________________________________     Soybeans                                                                               0   9G,4C                                                                               4G,2C                                                                               10G,7C                                                                              8G,3C                                                                              10G,7C                                                                              10G,7C                                                                              10G,7C                                                                              10G,6C                                                                              10G,7C                      Velvetleaf                                                                             8G,3C                                                                              9G,4C                                                                               8G,3C                                                                               10G,7C                                                                              8G,3C                                                                              10G,6C                                                                              10G,8C                                                                              8G   10G,7C                                                                              10G,3C                      Sesbania                                                                               5G,3C                                                                              7G,3C                                                                               7G,3C                                                                               10G,5C                                                                              9G,5C                                                                              9G,5C                                                                               10G,8C                                                                              10G,8C                                                                              10G,8C                                                                              10G,8C                      Cassia  4G,2C                                                                              9G,3C                                                                               6G,2C                                                                               10G,6C                                                                              5G,3C                                                                              10G,4C                                                                              10G,6C                                                                              9G,5C                                                                               10G,7C                                                                              10G,7C                      Cotton  3G,2C                                                                              7G,3C                                                                               5G,3C                                                                               9G,6C                                                                               8G,4C                                                                              9G,4C                                                                               10G,6C                                                                              7G,3C                                                                               9G,3C                                                                               10G,6C                      Morningglory                                                                           9G,4C                                                                              10G,7C                                                                              10G,7C                                                                              10G,8C                                                                              9G,5C                                                                              10G,8C                                                                              10G,8C                                                                              10G,6C                                                                              10G,7C                                                                              10G,7C                      Alfalfa 2C,3G                                                                              5G,2C                                                                               2C,3G                                                                               8G,5C                                                                               5G,3C                                                                              7G,4C                                                                               8G,6C                                                                               8G,4C                                                                               6G,2C                                                                               8G,3C                       Jimsonweed                                                                             1C  3G,2C                                                                               4G,2C                                                                               7G,3C                                                                               1G,1C                                                                              7G,3C                                                                               9G,4C                                                                               0    1G   4G,1C                       Cocklebur                                                                              1C  10G,6C                                                                              6G,3C                                                                               10G,7C                                                                              6G,2C                                                                              9G,3C                                                                               10G,7C                                                                              9G,6C                                                                               10G,9C                                                                              10G,7C                      Corn    1H  0    2G,1C                                                                               1G,2H                                                                               7G,4H                                                                              1H   6G,3C                                                                               3G,2H                                                                               0    4G,4H                       Crabgrass                                                                              1G  0    1G   4G   2G  4G   6G   1G   7G   2G                          Rice    7G,2C                                                                              8G,3C                                                                               8G,5C                                                                               9G,6C                                                                               8G,3C                                                                              8G,3C                                                                               8G,5C                                                                               8G,5C                                                                               9G,6C                                                                               8G,7C                       Nutsedge                                                                               2G  3G,3C                                                                               2G,1C                                                                               6G,2C                                                                               4G,1C                                                                              5G,1C                                                                               7G   5G,2C                                                                               6G,2C                                                                               7G,3C                       Barnyardgrass                                                                          1C,6G                                                                              7G,3C                                                                               1C,6G                                                                               10C  6G,2C                                                                              8G,5C                                                                               9G,7C                                                                               6G,3C                                                                               10C  8G,5C                       Wheat   0   1G   2G   3G   1G  2G   2G   1G   2G   4G                          Giant Foxtail                                                                          --  7G,2C                                                                               2G   9C   5G  7G,3C                                                                               8G,3C                                                                               5G,1C                                                                               8G,3C                                                                               6G,1C                       Wild Oats                                                                              6G  7G,2C                                                                               7G   7G,10C                                                                              7G  8G   8G   5G   7G,1C                                                                               7G,2C                       Sorghum 8G,1C                                                                              9G,3C                                                                               8G,4C                                                                               10C  8G,1U                                                                              9C   9C   9G,3C                                                                               10G,8C                                                                              9G,4C                       __________________________________________________________________________             Compound No. 9                                                                          Compound No. 10      Compound No. 11                          kg/ha   0.125    0.016                                                                               0.031 0.063                                                                               0.125                                                                               0.016 0.031 0.125                        __________________________________________________________________________     Soybeans                                                                               10G,8C   0    0     1G,1C                                                                               5G,3C                                                                               1C    10G,7C                                                                               10G,7C                       Velvetleaf                                                                             10G,9C   8G,3C                                                                               6C,3C 8G,3C                                                                               7G,3C                                                                               8G,3C 10G,8C                                                                               10G,9C                       Sesbania                                                                               10G,9C   2C   7G,3C 4G,3C                                                                               7G,3C                                                                               10G,6C                                                                               10G,7C                                                                               10G,9C                       Cassia  10G,7C   2C   10G,8C                                                                               4G,3C                                                                               7G,3C                                                                               8G,3C 7G,4C 9G,5C                        Cotton  10G,7C   3G,2C                                                                               7G,3C 5G,3C                                                                               8G,3C                                                                               6G,3C 10G,7C                                                                               10G,7C                       Morningglory                                                                           10G,8C   8G,3C                                                                               10G,4C                                                                               9G,3C                                                                               10G,6C                                                                              10G,4C                                                                               10G,8C                                                                               10G,9C                       Alfalfa 7G,4C    2C   7G,4C 3G,2C                                                                               8G,4C                                                                               7G,4C 7G,7C 9G,8C                        Jimsonweed                                                                             1G       5G,2C                                                                               7G,3C 5G,2C                                                                               7G,3C                                                                               3G,1C 9G,7C 10G,7C                       Cocklebur                                                                              10G,9C   1C   9G,3C 3G,2C                                                                               10G,5C                                                                              10G,7C                                                                               10G,8C                                                                               10G,8C                       Corn    1G,1H    2H,1C                                                                               6G,5H 3G,2H                                                                               7G,3U                                                                               9G,4C 10G,6C                                                                               10G,6C                       Crabgrass                                                                              9G,5C    1G   3G,1C 1G   6G,2C                                                                               0     8G,5C 8G,5C                        Rice    10G,7C   7G,1C                                                                               9G,3C 7G,1C                                                                               10G,7C                                                                              6G,2C 8G,6C 8G,6C                        Nutsedge                                                                               8G       2G   0     2G,1C                                                                               0    1G    1G    2G                           Barnyardgrass                                                                          10C      1G,1C                                                                               6G    1G,1C                                                                               8G,2C                                                                               6G,1C 8G,3C 10C                          Wheat   2G       0    1G    0    1G   0     0     1G                           Giant Foxtail                                                                          8G,4C    1G   6G,2C 3G,1C                                                                               7G,3C                                                                               3G    --    8G,3C                        Wild Oats                                                                              8G,2C    2G   7G    2G   7G   1G    8G,2C 8G,1C                        Sorghum 9C       8G,1C                                                                               9G,3C 8G,2U                                                                               9C   9G,2C 9C    9C                           __________________________________________________________________________             Compound No. 12                                                                               Compound No. 2                                                                               Compound No. 3                            kg/ha   0.016                                                                              0.031                                                                               0.125 0.016                                                                              0.031                                                                               0.125                                                                               0.016                                                                               0.031                                                                               0.063                                                                              0.125                       __________________________________________________________________________     Soybeans                                                                               0   7G,3C                                                                               10G,7C                                                                               5G,3C                                                                              9G,7C                                                                               10G,7C                                                                              6G,3C                                                                               10G,7C                                                                              9G,3C                                                                              9G,5C                       Velvetleaf                                                                             7G,3C                                                                              10G,8C                                                                              10G,8C                                                                               6G,3C                                                                              9G,5C                                                                               10G,9C                                                                              5G,3C                                                                               10G,7C                                                                              8G,3C                                                                              10G,9C                      Sesbania                                                                               6G,3C                                                                              10G,8C                                                                              10G,8C                                                                               5G,3C                                                                              9G,4C                                                                               10G,8C                                                                              5G,3C                                                                               10G,8C                                                                              7G,3C                                                                              10G,8C                      Cassia  4G,3C                                                                              10G,7C                                                                              10G,4C                                                                               3G,2C                                                                              10G,6C                                                                              10G,8C                                                                              4G,3C                                                                               10G,8C                                                                              5G,3C                                                                              10G,8C                      Cotton  4G,3C                                                                              10G,4C                                                                              10G,7C                                                                               3G,2C                                                                              7G,4C                                                                               10G,7C                                                                              3C   8G,5C                                                                               7G,2C                                                                              8G,7C                       Morningglory                                                                           9G,3C                                                                              10G,7C                                                                              10G,9C                                                                               6G,2C                                                                              10G,5C                                                                              10G,9C                                                                              6G,3C                                                                               10G,9C                                                                              7G,3C                                                                              10G,8C                      Alfalfa 0   2G   5G,1C 4G,2C                                                                              7G,3C                                                                               7G,4C                                                                               7G,3C                                                                               8G,5C                                                                               7G,3C                                                                              8G,5C                       Jimsonweed                                                                             2G,1C                                                                              0    6G,1C 2G,1C                                                                              5G,2C                                                                               7G,3C                                                                               4G,1C                                                                               0    3G,1C                                                                              5G,1C                       Cocklebur                                                                              1C  10G,8C                                                                              10G,8C                                                                               5G,2C                                                                              9G,4C                                                                               10G,7C                                                                              5G,2C                                                                               10G,7C                                                                              7G,4C                                                                              10G,7C                      Corn    9G,2C                                                                              9G,3U                                                                               10G,8U                                                                               0   2G   3G   0    0    2G,1C                                                                              0                           Crabgrass                                                                              0   3G   7G,4C 1G,1C                                                                              1G   3G   1G   0    3G  6G,1C                       Rice    4G  7G,2C                                                                               8G,3C 4G  5G,2C                                                                               7G,3C                                                                               5G,1C                                                                               3G,3C                                                                               8G,1C                                                                              5G,4C                       Nutsedge                                                                               4G  2G   3G    3G  6G,1C                                                                               7G,1C                                                                               2G   7G,3C                                                                               3G  6G                          Barnyardgrass                                                                          3G  7G,3C                                                                               8G,4C 5G,1C                                                                              8G,3C                                                                               9G,4C                                                                               4G,1C                                                                               8G   6G,1C                                                                              8G,3C                       Wheat   0   0    0     0   3G   4G   0    0    0   0                           Giant Foxtail                                                                          0   3G,1C                                                                               6G,2C 0   6G,2C                                                                               7G,1C                                                                               3G   7G,3C                                                                               3G  8G,1C                       Wild Oats                                                                              0   3G   7G    0   4G   7G,2C                                                                               0    4G,1C                                                                               5G  3G                          Sorghum 8G  9G,7C                                                                               9C    8G,1C                                                                              10G  10G,2U                                                                              9G   7G,3C                                                                               9G,2U                                                                              8G,3C                       __________________________________________________________________________             Compound No. 5 Compound No. 6                                                                               Compound No. 13                           hg/ha   0.016                                                                              0.031                                                                               0.125 0.016                                                                              0.031                                                                               0.125                                                                               0.016                                                                               0.031                                                                              0.062                                                                               0.125                       __________________________________________________________________________     Soybeans                                                                               6G,3C                                                                              9G,5C                                                                               10G,7C                                                                               7G,3C                                                                              10G,7C                                                                              10G,8C                                                                              3G   3G  7G,1C                                                                               7G,2C                       Velvetleaf                                                                             8G,3C                                                                              9G,4C                                                                               10G,7C                                                                               7G,3C                                                                              9G,4C                                                                               10G,7C                                                                              7G,2C                                                                               7G,2C                                                                              9G,3C                                                                               9G,4C                       Sesbania                                                                               5G,3C                                                                              9G,5C                                                                               10G,7C                                                                               4G,3C                                                                              8G,4C                                                                               10G,8C                                                                              7G,3C                                                                               8G,4C                                                                              9G,4C                                                                               9G,4C                       Cassia  4G,3C                                                                              10G,8C                                                                              10G,8C                                                                               4G,3C                                                                              10G,7C                                                                              10G,8C                                                                              8G,4C                                                                               9G,5C                                                                              9G,6C                                                                               10G,5C                      Cotton  5G,2C                                                                              9G,2C                                                                               10G,6C                                                                               6G,3C                                                                              9G,3C                                                                               10G,6C                                                                              1C   4G,3C                                                                              7G,3C                                                                               7G,4C                       Morningglory                                                                           7G,3C                                                                              10G,7C                                                                              10G,7C                                                                               8G,3C                                                                              10G,7C                                                                              10G,8C                                                                              8G,4C                                                                               8G,4C                                                                              9G,5C                                                                               9G,5C                       Alfalfa 4G,3C                                                                              7G,3C                                                                               7G,4C 4G,2C                                                                              6G,2C                                                                               8G,4C                                                                               2C   4G,2C                                                                              5G,2C                                                                               6G,2C                       Jimsonweed                                                                             5G,2C                                                                              6G,3C                                                                               8G,3C 2G,2C                                                                              7G,1C                                                                               8G,2C                                                                               3G   --  6G   8G                          Cocklebur                                                                              7G,3C                                                                              9G,4C                                                                               10G,7C                                                                               1C  10G,6C                                                                              10G,8C                                                                              4G,3C                                                                               6G,3C                                                                              7G,4C                                                                               10G,3C                      Corn    9G,3C                                                                              8G,6H                                                                               8G,8H 9G,3C                                                                              8G,4C                                                                               9G,4C                                                                               4H   8G,4H                                                                              9G,4C                                                                               9G,3U                       Crabgrass                                                                              0   2G   3G    0   1G   6G   0    0   2G   2G                          Rice    4G  5G,2C                                                                               7G,3C 4G,1C                                                                              4G,2C                                                                               7G,3C                                                                               2G   2G  5G   6G                          Nutsedge                                                                               1G  3G   4G    0   2G   3G   0    1G  2G   5G                          Barnyardgrass                                                                          6G,1C                                                                              8G,4C                                                                               9G,4C 0   8G,2C                                                                               8G,4C                                                                               0    3G  5G,3C                                                                               5G,3C                       Wheat   0   3G   3G    0   0    2G   0    1G  2G   3G                          Giant Foxtail                                                                          3G  4G   6G    0   7G,1C                                                                               7G   2G   2G  4G   4G                          Wild Oats                                                                              1G  2G   3G,1C 0   2G   3G,1C                                                                               0    0   2G   2G                          Sorghum 9G,2C                                                                              9G,3U                                                                               9G,3U 8G,1C                                                                              9G,3U                                                                               9G,3U                                                                               4G   6G  7G   7G,3C                       Sunflower                            0    9G,7C                                                                              10G,8C                                                                              10G,8C                      Mustard                              9G,3C                                                                               9G,3C                                                                              9G,3C                                                                               9G,3C                       Sugarbeets                           1C   2C  4G,3C                                                                               5G,3C                       Bushbean                             0    0   0    0                           __________________________________________________________________________

TEST E

Two ten-inch in diameter plastic pans lined with polyethylene liners were filled with prepared Fallsington silt loam soil. One pan was planted with seeds of wheat (Triticum aestivum), barley (Hordeum vulgare), wild oats (Avena fatua), downy brome (Bromus tectorum), cheatgrass (Bromus secalinus), blackgrass (Alopecurus myosuroides), annual bluegrass (Poa annua), green foxtail (Setaria viridis), quackgrass (Agropyron repens), Italian ryegrass (Lolium multiflorum) and ripgut brome (Bromus rigidus). The other pan was planted with seeds of Russian thistle (Salsola kali), tansy mustard (Descuraina pinnata), smartweed (Polygonum pennsylvanicum), jimhill or tumble mustard (Sisymbrium altissium) kochia (Kochia scoparia), shepard's purse (Capsella bursa-pastoris), Matricaria inodora, black nightshade (Solanum migrum), yellow rocket (Barbarea vulgaris), wild mustard (Brassica kaber) and wild buckwheat (Polygonum convolvulus). The above two pans were treated pre-emergence. At the same time two pans in which the above plant species were growing were treated post-emergence. Plant height at the time of treatment ranged from 1-15 cm depending on plant species.

The compounds applied were diluted with a nonphytotoxic solvent and sprayed over-the-top of the pans. An untreated control and a solvent-alone control were included for comparison. All treatments were maintained in the greenhouse for 20 days at which time the treatments were compared to the controls and the effects visually rated in accordance with the previously described rating system. The recorded data are presented in Table E.

Several of the compounds included in this table provide excellent weed control at very low rates of application, yet are tolerated with little or no injury by wheat and barley at rates which are multiples of those required for weed control. This observation applies to both pre- and post-emergence treatments.

                                      TABLE E                                      __________________________________________________________________________              Compound No. 2    Compound No. 3                                      kg/ha    0.02 0.06                                                                               0.02 0.06                                                                               0.02 0.06                                                                               0.02 0.06                                                                               0.02 0.06                                                                               0.02 0.06                TEST PLANT                                                                              Pre-Emergence                                                                           Post-Emergence                                                                          Pre-Emegence                                                                            Post-Emergence                                                                          Pre-Emergence                                                                           Post-Emergence           __________________________________________________________________________     Wheat    0    0   0    1G  0    1G  0    1C,1G                                                                              0    2C,1G                                                                              0    1C,2G               Barley   2C,4G                                                                               5C,6G                                                                              1G   4C,6G                                                                              3G   3C,7G                                                                              6C,5G                                                                               7C,7G                                                                              5G   3C,8G                                                                              5C,7G                                                                               8C,7G               Wild Oats                                                                               3C,2G                                                                               5C,5G                                                                              1G   6C,6G                                                                              3G   5C,7G                                                                              1C,2G                                                                               5C,6G                                                                              1C,5G                                                                               5C,7G                                                                              4C,5G                                                                               6C,6G               Downy Brome                                                                             7C,4G                                                                               8C,7G                                                                              2C,2G                                                                               10C 7C,7G                                                                               10C 7C 7G                                                                               10C 6C,7G                                                                               10C 7C,8G                                                                               10C                 Cheatgrass                                                                              6C,5G                                                                               10C 3C,5G                                                                               8C,7G                                                                              10C  10C 9C,8G                                                                               10C 9C,8G                                                                               10C 10C  10C                 Blackgrass                                                                              7C,7G                                                                               10C 5C,5G                                                                               7C,7G                                                                              10C  10C 10C  10C 10C  10C 10C  10C                 Annual Bluegrass                                                                        3G   6C,7G                                                                              4G   6C,7G                                                                              7C,7G                                                                               7C,8G                                                                              7C,6G                                                                               9C,7G                                                                              5C,6G                                                                               9C,9G                                                                              9C   10C                 Green Foxtail                                                                           4C,2G                                                                               6C,6G                                                                              2G   6C,6G                                                                              7C,6G                                                                               7C,8G                                                                              3C,6G                                                                               7C,7G                                                                              3C,4G                                                                               9C,9G                                                                              6C,6G                                                                               7C,6G               Quackgrass                                                                              3G   4C,6G                                                                              2C,4G                                                                               3C,7G                                                                              7G   5C,8G                                                                              1C,6G                                                                               5C,7G                                                                              5C,6G                                                                               9C,8G                                                                              3C,6G                                                                               8C,7G               Italian Ryegrass                                                                        2G   2C,5G                                                                              3G   6G  6G   2C,7G                                                                              2G   2C,4G                                                                              3G   4C,6G                                                                              1C,3G                                                                               4C,5G               Ripgut Brome                                                                            2C,4G                                                                               6C,7G                                                                              1G   2C,4G                                                                              3C,7G                                                                               4C,8G                                                                              1C,2G                                                                               3C,5G                                                                              3G   5C,7G                                                                              3C,4G                                                                               6C,7G               Russian Thistle                                                                         9C,8G                                                                               9C,9G                                                                              2C,2G                                                                               5C,7G                                                                              4C,5G                                                                               7C,7G                                                                              2C,3G                                                                               10C --   --  --   --                  Tansy Mustard                                                                           10C  10C 10C  10C 10C  10C 10C  10C 10C  10C 10C  10C                 Smartweed                                                                               --   --  --   --  --   --  --   --  --   --  --   --                  Jimhill Mustard                                                                         10C  10C 10C  10C 10C  10C 10C  10C 10C  10C 10C  10C                 Kochia   4G   2C,5G                                                                              7C,6G                                                                               7C,7G                                                                              6G   3C,7G                                                                              2G   2C,4G                                                                              2C,5G                                                                               5C,6G                                                                              0    2G                  Shepherd's Purse                                                                        10C  10C 7C,7G                                                                               8C,7G                                                                              7C,7G                                                                               9C,9G                                                                              9C,8G                                                                               10C 10C  10C 10C  10C                 False Chamomile                                                                         4C,6G                                                                               7C,8G                                                                              5C,5G                                                                               7C,7G                                                                              9C,9G                                                                               9C,9G                                                                              9C,9G                                                                               10C 8C,8G                                                                               9C,9G                                                                              10C  10C                 Black Nightshade                                                                        1C,7G                                                                               2C,8G                                                                              3G   1C,5G                                                                              7C,8G                                                                               7C,8G                                                                              7C,8G                                                                               10C 3C,6G                                                                               5C,6G                                                                              9C,8G                                                                               10C                 Yellow Rocket                                                                           9C,9G                                                                               9C,9G                                                                              5C,6G                                                                               10C 9C,9G                                                                               9C,9G                                                                              10C  10C 9C,9G                                                                               10C 10C  10C                 Wild Mustard                                                                            8C,8G                                                                               9C,9G                                                                              10C  10C 7C,8G                                                                               9C,9G                                                                              10C  10C 9C,8G                                                                               9C,9G                                                                              10C  10C                 Wild Buckwheat                                                                          3G   4C,4G                                                                              2C,2G                                                                               5C,5G                                                                              3C,4G                                                                               4C,5G                                                                              1C,2G                                                                               4C,4G                                                                              2C,4G                                                                               5C,6G                                                                              3C,4G                                                                               4C,4G               Matricaria inodora                                                             __________________________________________________________________________              Compound No. 3                                                        kg/ha     0.02                                                                              0.06                                                                               0.02 0.06                                                                               0.002                                                                              0.02 0.12                                                                               0.002                                                                              0.02                                                                               0.12                                                                               0.002                                                                              0.02                                                                               0.12*               TEST PLANT                                                                              Pre-Emergence                                                                          Post-Emergence                                                                          Pre-Emergence                                                                               Post-Emergence                                                                             Pre-Emergence               __________________________________________________________________________     Wheat    0   1C,1G                                                                              0    0   0   0    0   0   1G  3G  0   0   0                   Barley   5G  6C,7G                                                                              4C,6G                                                                               8C,8G                                                                              0   0    3G  0   3G  6G  0   0   3G                  Wild Oats                                                                               5G  4C,6G                                                                              1G   1C,2G                                                                              0   0    1C,3G                                                                              0   1G  1C,5G                                                                              0   0   3G                  Downy Brome                                                                             7C,7G                                                                              10C 6C,5G                                                                               7C,8G                                                                              1G  2C,3G                                                                               3C,5G                                                                              2G  4C,5G                                                                              6C,5G                                                                              3G  3G  4C,6G               Cheatgrass                                                                              10C 10C 8C,7G                                                                               8C,8G                                                                              2G  6C,7G                                                                               7C,8G                                                                              5C,6G                                                                              7C,6G                                                                              7C,6G                                                                              2C,4G                                                                              4C,6G                                                                              7C,7G               Blackgrass                                                                              10C 10C 9C,8G                                                                               10C 1C,4G                                                                              7C,7G                                                                               10C 6C,6G                                                                              10C 10C 1C,6G                                                                              5C,6G                                                                              10C                 Annual Bluegrass                                                                        7C,8G                                                                              7C,8G                                                                              4C,6G                                                                               7C,8G                                                                              2G  1C,4G                                                                               4C,6G                                                                              1C,4G                                                                              7C,7G                                                                              8C,8G                                                                              2G  1C,3G                                                                              4C,6G               Green Foxtail                                                                           5C,6G                                                                              8C,8G                                                                              2C,2G                                                                               3C,3G                                                                              0   1C,1G                                                                               3C,6G                                                                              0   2C,3G                                                                              8C,8G                                                                              0   3C,4G                                                                              4C,7G               Quackgrass                                                                              7C,6G                                                                              9C,8G                                                                              5C,6G                                                                               5C,7G                                                                              0   2G   2C,6G                                                                              0   2G  1C,3G                                                                              1G  3G  2C,6G               Italian Ryegrass                                                                        3G  1C,7C                                                                              1G   3G  0   1G   1C,4G                                                                              0   0   2G  0   2G  1C,3G               Ripgut Brome                                                                            2C,6G                                                                              7C,7G                                                                              2C,5G                                                                               3C,6G                                                                              0   0    5G  0   2G  1C,5G                                                                              0   2G  3G                  Russian Thistle                                                                         0   2C,2G                                                                              10C  10C 0   0    1C,2G                                                                              2C,2G                                                                              3C,4G                                                                              7C,7G                                                                              0   0   1C,2G               Tansy Mustard                                                                           9C,9G                                                                              10C 10C  10C 8C,8G                                                                              8C,8G                                                                               9C,9G                                                                              8C,7G                                                                              10C 10C 5C,6G                                                                              9C,9G                                                                              9C,9G               Smartweed                                                                               --  --  --   --  --  --   --  --  --  --  --  --  --                  Jimhill Mustard                                                                         9C,9G                                                                              10C 10C  10C 2C,3G                                                                              7C,8G                                                                               9C,9G                                                                              10C 10C 10C 7C,7G                                                                              9C,8G                                                                              9C,9G               Kochia   5G  3C,8G                                                                              3C,2G                                                                               2C,4G                                                                              0   2G   3G  0   0   1G  0   1G  2C,3G               Shepherd's Purse                                                                        9C,9G                                                                              9C,9G                                                                              8G,7G                                                                               8C,8G                                                                              3C,5G                                                                              9C,9G                                                                               9C,9G                                                                              10C 9C,8G                                                                              10C 8C,8G                                                                              9C,9G                                                                              10C                 False Chamomile                                                                         8C,9G                                                                              9C,9G                                                                              9C,8G                                                                               10C                                                      Black Nightshade                                                                        2C,7G                                                                              4C,7G                                                                              5C,6G                                                                               7C,7G                                                                              0   1C,3G                                                                               3C,6G                                                                              2C,3G                                                                              2C,4G                                                                              4C,7G                                                                              1C,4G                                                                              3C,5G                                                                              5C,6G               Yellow Rocket                                                                           8C,8C                                                                              9C,8G                                                                              10C  10C 2C,4G                                                                              3C,8G                                                                               7C,9G                                                                              10C 10C 10C 4C,7G                                                                              7C,8G                                                                              7C,8G               Wild Mustard                                                                            8C,8G                                                                              9C,8G                                                                              10C  10C 3C,4G                                                                              7C,7G                                                                               8C,8G                                                                              10C 10C 10C 7C,7G                                                                              7C,7G                                                                              8C,8G               Wild Buckwheat                                                                          4G  3C,6G                                                                              1C,5G                                                                               5C,6G                                                                              1C,1G                                                                              2G   3C,4G                                                                              2C,2G                                                                              3C,4G                                                                              3C,4G                                                                              1G  1C,1G                                                                              2C,3G               Matricaria inodora        3C,4G                                                                              7C,7G                                                                               7C,8G                                                                              9C,7G                                                                              9C,8G                                                                              10C 6C,5G                                                                              7C,7G                                                                              8C,8G               __________________________________________________________________________                                                            Compound                         Compound No. 3                                                                             Compound No. 5                    6                       kg/ha    0.002                                                                              0.02                                                                               0.12*                                                                              0.02                                                                               0.06                                                                               0.02 0.06                                                                               0.02                                                                               0.06                                                                               0.02 0.06                                                                               0.02                                                                               0.06                TEST PLANT                                                                              Post-Emergence                                                                             Pre-Emergence                                                                          Post-Emergence                                                                          Pre-Emergence                                                                          Post-Emergence                                                                          Pre-Emergence           __________________________________________________________________________     Wheat    0   1G  2G  0   0   0    0   0   1C,1G                                                                              0    0   0   0                   Barley   0   2G  2C,4G                                                                              1G  3G  0    1C,2G                                                                              0   2C,7G                                                                              0    2C,5G                                                                              0   2G                  Wild Oats                                                                               0   1G  1G  0   2C,5G                                                                              0    2G  1C,2G                                                                              2C,5G                                                                              0    1C,2G                                                                              0   3G                  Downy Brome                                                                             2G  3G  4C,5G                                                                              1C,2G                                                                              5C,7G                                                                              0    3C,3G                                                                              4G  4C,7G                                                                              2G   7C,7G                                                                              2G  2C,6G               Cheatgrass                                                                              4G  1C,5G                                                                              8C,5G                                                                              2C,6G                                                                              6C,7G                                                                              2G   7C,8G                                                                              4C,7G                                                                              5C,7G                                                                              2C,3G                                                                               10C 3G  4C,7G               Blackgrass                                                                              3C,4G                                                                              5C,5G                                                                              10C 7C,8G                                                                              7C,8G                                                                              7C,5G                                                                               10C 10C 7C,8G                                                                              7C,6G                                                                               10C 3C,4G                                                                              7C,7G               Annual Bluegrass                                                                        1C,4G                                                                              5C,6G                                                                              10C 1C,6C                                                                              7G  2G   7C,6C                                                                              6G  7G  1C,2G                                                                               9C  3G  2C,7G               Green Foxtail                                                                           0   3G  6C,6G                                                                              2C,3G                                                                              3C,6G                                                                              0    3C,4G                                                                              1G  3C,4G                                                                              0    6C,5G                                                                              1G  1C,3G               Quackgrass                                                                              0   3G  4G  3G  5G  0    3C,5G                                                                              0   2C,7G                                                                              0    2C,4G                                                                              0   5G                  Italian Ryegrass                                                                        0   1G  1C,3G                                                                              2G  4G  0    3G  0   2C,7G                                                                              0    1C,3G                                                                              0   2G                  Ripgut Brome                                                                            0   2G  2C,4G                                                                              1C,2G                                                                              2C,3G                                                                              0    1C,2G                                                                              0   3C,3G                                                                              0    2C,2G                                                                              0   1G                  Russian Thistle                                                                         0   2C,3G                                                                              2C,3G                                                                              3G  7C,7G                                                                              10C  10C --  --  --   --  2C,3G                                                                              7C,8G               Tansy Mustard                                                                           7C,7G                                                                              10C 10C 10C 10C 10C  10C 10C 10C 10C  10C 10C 10C                 Smartweed                                                                               --  --  --  --  --  --   --  --  --  --   --  --  --                  Jimhill Mustard                                                                         10C 10C 10C 8C,9G                                                                              9C,9G                                                                              10C  10C 2C,6G                                                                              10C 10C  10C 10C 10C                 Kochia   0   1G  2C,2G                                                                              1C,6G                                                                              5C,7G                                                                              7C,8G                                                                               10C 2C,4G                                                                              5C,6G                                                                              7C,7G                                                                               10C 2G  2C,5G               Shepherd's Purse                                                                        10C 8C,8G                                                                              9C,8G                                                                              8C,8G                                                                              10C 8C,8G                                                                               10C 1C,5G                                                                              10C 10C  10C 8C,9G                                                                              9C,9G               False Chamomile      2G  6C,7G                                                                              7C,7G                                                                               10C 3G  5C,8G                                                                              7C,6G                                                                               10C 2G  5C,6G               Black Nightshade                                                                        2C,2G                                                                              3C,3G                                                                              4C,5G                                                                              6G  6C,7G                                                                              6C,7G                                                                               10C 1C,2G                                                                              4C,7G                                                                              4C,6G                                                                               10C 1C,6G                                                                              5C,7G               Yellow Rocket                                                                           7C,7G                                                                              8C,7G                                                                              8C,8G                                                                              8C,8G                                                                              9C,9G                                                                              8C,8G                                                                               10C 7G  10C 10C  10C 7G  4C,7G               Wild Mustard                                                                            10C 10C 10C 4C,7G                                                                              9C,9C                                                                              10C  10C 9C,9G                                                                              9C,9G                                                                              10C  10C 5G  8C,8G               Wild Buckheat                                                                           1C,2G                                                                              2C,3G                                                                              3C,4G                                                                              3C,6G                                                                              5C,7G                                                                              4C,5G                                                                               10C 3C,5G                                                                              5C,6G                                                                              6C,6G                                                                               10C 2G  2C,3G               Matricaria inodora                                                                      6C,5G                                                                              8C,8G                                                                              9C,8G                                                         __________________________________________________________________________              Compound No. 6             Compound No. 8    Compound No. 9           kg/ha    0.02 0.06                                                                               0.02                                                                               0.06 0.02 0.06                                                                               0.02                                                                               0.06 0.02 0.06                                                                               0.02 0.06                TEST PLANT                                                                              Post-Emergence                                                                          Pre-Emergence                                                                           Post-Emergence                                                                          Pre-Emergence                                                                           Post-Emergence                                                                          Pre-Emergence            __________________________________________________________________________     Wheat    0    0   0   1C,1G                                                                               0    0   1C,1G                                                                              3C,1G                                                                               2G   2C,3G                                                                              1C,2G                                                                               2C,2G               Barley   0    1G  0   2C,3G                                                                               2G   1C,3G                                                                              2C,6G                                                                              3C,7G                                                                               6C,6G                                                                               7C,8G                                                                              3C,7G                                                                               6C,8G               Wild Oats                                                                               0    1G  0   3C,4G                                                                               0    2G  6C,6G                                                                              6C,6G                                                                               4C,5G                                                                               8C,8G                                                                              3C,7G                                                                               6C,7G               Downy Brome                                                                             1C,2G                                                                               3C,5G                                                                              2G  7C,7G                                                                               2G   3C,4G                                                                              8C,8G                                                                              9C,9G                                                                               7C,8G                                                                               10C 8C,7G                                                                               10C                 Cheatgrass                                                                              1C,3G                                                                               5C,7G                                                                              1C,7G                                                                              7C,8G                                                                               1C,3G                                                                               10C 10C 10C  8C,8G                                                                               10C 10C  10C                 Blackgrass                                                                              5C,6G                                                                               7C,8G                                                                              3C,7G                                                                              10C  3C,4G                                                                               8C,7G                                                                              10C 10C  8C,8G                                                                               10C 10C  10C                 Annual Bluegrass                                                                        3G   4G  6G  7G   1G   2C,2G                                                                              8C,7G                                                                              8C,8G                                                                               7C,7G                                                                               9C,8G                                                                              7C,7G                                                                               9C,8G               Green Foxtail                                                                           0    1C,2G                                                                              2G  4C,6G                                                                               1C,2G                                                                               2C,3G                                                                              7C,6G                                                                              7C,8G                                                                               4C,3G                                                                               7C,6G                                                                              7C,7G                                                                               7C,8G               Quackgrass                                                                              0    2C,3G                                                                              2C,3G                                                                              3C,6G                                                                               1G   1C,2G                                                                              4C,6G                                                                              8C,8G                                                                               7C,7G                                                                               7C,7G                                                                              8G   8C,8G               Italian Ryegrass                                                                        0    0   1C,2G                                                                              2C,3G                                                                               1G   1C,2G                                                                              3C,6G                                                                              8C,8G                                                                               4C,6G                                                                               5C,7G                                                                              2C,8G                                                                               7C,8G               Ripgut Brome                                                                            0    0   1G  1C,2G                                                                               2G   1C,3G                                                                              5C,7G                                                                              6C,8G                                                                               3C,5G                                                                               5C,7G                                                                              8G   7C,8G               Russian Thistle                                                                         10C  10C --  --   --   --  2C,4G                                                                              10C  8C,7G                                                                               9C,8G                                                                              2G   5C,5G               Tansy Mustard                                                                           10C  10C 10C 10C  10C  10C 10C 10C  10C  10C 10C  10C                 Smartweed                                                                               --   --  --  --   --   --  --  --   --   --  --   --                  Jimhill Mustard                                                                         10C  10C 3C,6G                                                                              10C  8C   10C 9C,9G                                                                              10C  10C  10C 10C  10C                 Kochia   3C,4G                                                                               4C,7G                                                                              2G  2C,4G                                                                               0    5C,6G                                                                              5C,6G                                                                              5C,7G                                                                               4G   4C,5G                                                                              7G   3C,8G               Shepherd's Purse                                                                        7C,7G                                                                               10C 5C,6G                                                                              10C  10C  10C 9C,9G                                                                              10C  9C,7G                                                                               10C 10C  10C                 False Chamomile                                                                         5C,6G                                                                               10C 1G  7C,8G                                                                               8C,8G                                                                               9C,8G                                                                              7C,8G                                                                              8C,9G                                                                               9C,8G                                                                               10C 7C,8G                                                                               9C,9G               Black Nightshade                                                                        2C,6G                                                                               9C,8C                                                                              1C,2G                                                                              2C,4G                                                                               2C,4G                                                                               7C,8G                                                                              2C,7G                                                                              3C,8G                                                                               5G   6G  5C,8G                                                                               6C,8G               Yellow Rocket                                                                           0    2G  6G  7G   0    2C,4G                                                                              9C,9G                                                                              9C,9G                                                                               9C,7G                                                                               9C,8G                                                                              9C,9G                                                                               10C                 Wild Mustard                                                                            2C,3G                                                                               7C,6G                                                                              2C,5G                                                                              3C,6G                                                                               8C,8G                                                                               7C,6G                                                                              9C,9G                                                                              9C,9G                                                                               10C  10C 9C,9G                                                                               9C,9G               Wild Buckwheat                                                                          1C,2G                                                                               4C,5G                                                                              2C,4G                                                                              2C,5G                                                                               2C,2G                                                                               5C,5G                                                                              2C,4G                                                                              5C,6G                                                                               7C,5G                                                                               7C,7G                                                                              4C,6G                                                                               5C,7G               Matricaria inodora                                                             __________________________________________________________________________               Compound No. 9                                                                            Compound No. 11      Compound No. 12                      kg/ha     0.02  0.06 0.02 0.06 0.02  0.06 0.02 0.06 0.02  0.06                 TEST PLANT                                                                               Post-Emergence                                                                            Pre-Emergence                                                                            Post-Emergence                                                                            Pre-Emergence                                                                            Post-Emergence             __________________________________________________________________________     Wheat     1C,2G 2C,2G                                                                               0    0    0     1C,4G                                                                               0    0    0     0                    Barley    8C,7G 8C,8G                                                                               2C,2G                                                                               2C,4G                                                                               0     3C,3G                                                                               2G   3G   0     2G                   Wild Oats 3C,4G 5C,6G                                                                               2C,3G                                                                               3C,6G                                                                               0     6C,7G                                                                               3G   6G   0     1C,3G                Downy Brome                                                                              8C,8G 10C  4C,6G                                                                               7C,7G                                                                               2C,2G 10C  2C,5G                                                                               3C,6G                                                                               2G    5C,4G                Cheatgrass                                                                               10C   10C  3C,7G                                                                               10C  2C,6G 9C,8G                                                                               1C,7G                                                                               7C,7G                                                                               3G    2C,6G                Blackgrass                                                                               10C   10C  7C,8G                                                                               10C  3C,7G 10C  5C,7G                                                                               8C,8G                                                                               2C,2G 5C,7G                Annual Bluegrass                                                                         10C   10C  7G   7C,8G                                                                               7C,7G 10C  5G   4C,7G                                                                               2G    3G                   Green Foxtail                                                                            6C,7G 7C,8G                                                                               2C,4G                                                                               5C,8G                                                                               3G    7C,7G                                                                               1C,2G                                                                               2C,5G                                                                               0     1G                   Quackgrass                                                                               7C,6G 9C,7G                                                                               6G   4C,7G                                                                               1C,4G 5C,7G                                                                               2G   5G   0     1C,2G                Italian Ryegrass                                                                         10C   10C  7G   5C,8G                                                                               2C,4G 10C  3G   5G   0     3G                   Ripgut Brome                                                                             4C,6G 6C,7G                                                                               3C,3G                                                                               3C,6G                                                                               0     2C,3G                                                                               2G   3G   0     0                    Russian Thistle                                                                          6C,5G 10C  3C,3G                                                                               8C,7G                                                                               10C   10C  2C,2G                                                                               2C,3G                                                                               2C,3G 10C                  Tansy Mustard                                                                            10C   10C  10C  10C  10C   10C  10C  10C  10C   10C                  Smartweed --    --   --   --   --    --   --   --   --    --                   Jimhill Mustard                                                                          10C   10C  10C  10C  10C   10C  10C  10C  10C   10C                  Kochia    5C,6G 10C  3C,7G                                                                               5C,8G                                                                               5C,5G 10C  2C,5G                                                                               3C,6G                                                                               0     7C,7G                Shepherd's Purse                                                                         10C   10C  10C  10C  10C   10C  9C,9G                                                                               9C,9G                                                                               10C   10C                  False Chamomile                                                                          10C   10C  7C,7G                                                                               8C,8G                                                                               10C   10C  5C,6G                                                                               7C,8G                                                                               10C   10C                  Black Nightshade                                                                         8C,8G 10C  7C,8G                                                                               8C,8G                                                                               10C   10C  7C,7G                                                                               7C,8G                                                                               10C   10C                  Yellow Rocket                                                                            10C   10C  10C  9C,9G                                                                               10C   10C  7C,8G                                                                               7C,8G                                                                               0     1C,2G                Wild Mustard                                                                             10C   10C  9C,9G                                                                               9C,9G                                                                               10C   10C  9C,9G                                                                               9C,9G                                                                               10C   10C                  Wild Buckwheat                                                                           3C,3G 9C,8G                                                                               7C,7G                                                                               8C,8G                                                                               8C,7G 10C  7C,8G                                                                               7C,8G                                                                               4C,3G 8C,7G                Matricaria inodora                                                             __________________________________________________________________________      *80% wettable powder formulation                                         

TEST F

The results obtained from this test demonstrate the high herbicidal activity of a compound selected from the scope of the invention when it is mixed with the water of simulated rice paddies.

The test samples were applied directly into the water of paddies three days after transplanting of M7 rice plants. The test was maintained in a greenhouse, and plant response ratings were taken 34 days after application, utilizing the rating system as previously described.

                  TABLE F                                                          ______________________________________                                         Compound No. 3                                                                                   Barnyard-  Water                                             Treatment                                                                               Rice     grass      Chestnut                                                                              Arrowhead                                  ______________________________________                                         10 g/ha  6G       5E         8G     0                                          40 g/ha  10G,4C   10E        10G,3C 5F                                         ______________________________________                                    

TEST G

A field study was conducted to determine the crop selectivity and herbicidal activities of various chemicals. The test was conducted on a Wea silt loam having an organic matter content of 2.8 percent and a pH of 7.2.

The plots were planted to sugarbeets, oats, giant foxtail, wild oats, barley, rape, wheat, soybeans, velvetleaf, dry beans, corn and sunflower. The area had a natural infestation of pigweed.

The test included both pre- and post-emergence treatments. The pre-emergence treatments were applied directly after planting. The post-emergence treatments were applied 21 days after planting. Ratings were made on the percent control of both crops and weeds at various times after application.

Pre-Emergence Test - Table G-I

The n-propyl-dimethoxypyrimidine material showed crop selectivity on wheat, corn and soybeans while controlling giant foxtail, velvetleaf and pigweed at the selected rates. The isopropyl-dimethoxypyrimidin material exhibited crop selectivity on wheat and corn. The compound controls giant foxtail and pigweed.

Post-emergence test - Table G-II

The isopropyl-dimethoxypyrimidine compound exhibited selectivity in all of the cereal crops tested (oats, barley and wheat) while some corn tolerance was noted. The compound provided control of broadleaf weeds including velvetleaf and pigweed.

The n-propyldimethoxypyrimidine exhibited selectivity in wheat, oats, corn and soybeans; it controlled pigweed and velvetleaf.

                                      TABLE G-I                                    __________________________________________________________________________     PRE-EMERGENCE FIELD TEST                                                              Compound No. 9           Compound No. 3                                        kg ai/ha                 kg ai/ha                                              1/2      1/4     1/16    1/2      1/4      1/16                                *  +  o  * +  o  * +  o  *  +  o  *  +  o  *  +  o                      __________________________________________________________________________     Sugarbeets                                                                            8.0                                                                               8.5                                                                               7.0                                                                               9.0                                                                              9.0                                                                               9.0                                                                               8.0                                                                              8.0                                                                               6.0                                                                               9.0                                                                               10.0                                                                              10.0                                                                              9.0                                                                               9.5                                                                               8.5                                                                               9.5                                                                               9.0                                                                               8.0                    Oats   5.5                                                                               5.0                                                                               5.5                                                                               4.0                                                                              5.0                                                                               3.0                                                                               2.0                                                                              1.5                                                                               1.0                                                                               6.0                                                                               6.5                                                                               6.0                                                                               4.0                                                                               4.0                                                                               2.5                                                                               2.5                                                                               2.0                                                                               1.5                    Giant Foxtail                                                                         10.0                                                                              9.5                                                                               10.0                                                                              9.5                                                                              9.0                                                                               5.0                                                                               8.5                                                                              5.0                                                                               6.0                                                                               10.0                                                                              9.5                                                                               8.5                                                                               9.5                                                                               8.5                                                                               7.5                                                                               10.0                                                                              8.5                                                                               6.5                    Wild Oats                                                                             6.5                                                                               8.0                                                                               6.5                                                                               5.0                                                                              6.0                                                                               5.0                                                                               4.0                                                                              2.5                                                                               2.5                                                                               7.0                                                                               7.0                                                                               5.5                                                                               5.0                                                                               5.0                                                                               3.0                                                                               2.0                                                                               2.0                                                                               2.0                    Barley 7.5                                                                               8.5                                                                               8.0                                                                               5.0                                                                              6.0                                                                               2.5                                                                               5.0                                                                              4.0                                                                               2.5                                                                               6.0                                                                               7.0                                                                               4.0                                                                               7.0                                                                               6.5                                                                               4.0                                                                               4.5                                                                               4.5                                                                               3.0                    Rape   9.0                                                                               10.0                                                                              10.0                                                                              9.0                                                                              10.0                                                                              10.0                                                                              8.5                                                                              10.0                                                                              10.0                                                                              9.5                                                                               10.0                                                                              10.0                                                                              9.5                                                                               9.5                                                                               10.0                                                                              9.5                                                                               10.0                                                                              9.5                    Wheat  1.0                                                                               2.0                                                                               0.5                                                                               1.0                                                                              1.0                                                                               1.0                                                                               1.0                                                                              0.0                                                                               0.0                                                                               2.0                                                                               2.5                                                                               0.0                                                                               1.0                                                                               1.0                                                                               0.0                                                                               0.5                                                                               0.5                                                                               0.0                    Soybeans                                                                              6.0                                                                               3.0                                                                               5.5                                                                               3.5                                                                              0.5                                                                               1.0                                                                               2.0                                                                              1.0                                                                               0.0                                                                               8.0                                                                               8.0                                                                               9.0                                                                               3.5                                                                               2.5                                                                               2.5                                                                               5.0                                                                               2.0                                                                               3.5                    Velvetleaf                                                                            6.0                                                                               9.5                                                                               9.5                                                                               3.5                                                                              9.0                                                                               8.0                                                                               0.5                                                                              2.5                                                                               1.5                                                                               4.0                                                                               8.5                                                                               7.5                                                                               4.5                                                                               6.0                                                                               1.5                                                                               5.0                                                                               4.0                                                                               3.5                    Dry Beans                                                                             5.5                                                                               8.5                                                                               9.0                                                                               4.0                                                                              7.5                                                                               5.0                                                                               1.5                                                                              2.5                                                                               1.5                                                                               5.0                                                                               7.0                                                                               4.0                                                                               4.0                                                                               4.5                                                                               2.0                                                                               4.5                                                                               4.0                                                                               2.5                    Corn   3.0                                                                               2.5                                                                               4.0                                                                               1.0                                                                              0.5                                                                               1.0                                                                               1.5                                                                              0.0                                                                               1.0                                                                               4.5                                                                               4.0                                                                               3.5                                                                               1.0                                                                               1.0                                                                               1.5                                                                               3.0                                                                               0.5                                                                               0.5                    Sunflower                                                                             10.0                                                                              10.0                                                                              9.5                                                                               8.0                                                                              9.0                                                                               8.5                                                                               9.5                                                                              9.5                                                                               9.5                                                                               10.0                                                                              10.0                                                                              10.0                                                                              8.5                                                                               9.0                                                                               8.5                                                                               4.0                                                                               9.5                                                                               8.0                    Pigweed                                                                               10.0                                                                              10.0                                                                              10.0                                                                              9.5                                                                              10.0                                                                              9.5                                                                               9.5                                                                              10.0                                                                              9.5                                                                               10.0                                                                              10.0                                                                              10.0                                                                              1.00                                                                              10.0                                                                              9.5                                                                               10.0                                                                              10.0                                                                              9.0                    __________________________________________________________________________      * Averaged plant response of two replications taken 21 days after              treatment.                                                                     + Averaged plant response of two replications taken 38 days after              treatment.                                                                     o Averaged plant response of two replications taken 55 days after              treatment.                                                                     Rating Scale  0-10, 0 = no control, 10 = 100% control.                   

                                      TABLE G-II                                   __________________________________________________________________________     POST-EMERGENCE FIELD TEST                                                             Compound No. 3    Compound No. 9                                               kg ai/ha          kg ai/ha                                                     1/4                                                                               1/16                                                                              1/64                                                                              1/4                                                                               1/16                                                                              1/64                                                                              1/4                                                                               1/l6                                                                              1/64                                                                              1/4                                                                               1/l6                                                                              1/64                                          +  o  +  o  +  o  +  o  +  o  +  o                                      __________________________________________________________________________     Sugarbeets                                                                            8.5                                                                               6.5                                                                               8.5                                                                               6.0                                                                               5.5                                                                               2.5                                                                               7.5                                                                               4.0                                                                               9.0                                                                               6.5                                                                               6.0                                                                               4.5                                    Oats   2.5                                                                               1.5                                                                               2.0                                                                               1.0                                                                               0.5                                                                               0.0                                                                               4.0                                                                               1.0                                                                               3.0                                                                               0.5                                                                               2.0                                                                               0.5                                    Giant Foxtail                                                                         2.5                                                                               3.0                                                                               2.5                                                                               2.0                                                                               3.5                                                                               2.0                                                                               6.5                                                                               3.5                                                                               7.0                                                                               6.5                                                                               4.5                                                                               4.5                                    Wild Oats                                                                             3.5                                                                               1.0                                                                               2.5                                                                               0.5                                                                               2.5                                                                               0.0                                                                               4.0                                                                               1.0                                                                               4.0                                                                               1.5                                                                               2.5                                                                               1.0                                    Barley 6.5                                                                               1.5                                                                               3.0                                                                               1.0                                                                               2.5                                                                               2.0                                                                               7.0                                                                               4.0                                                                               4.5                                                                               2.0                                                                               3.5                                                                               2.0                                    Rape   9.0                                                                               l0.0                                                                              8.5                                                                               8.0                                                                               7.5                                                                               4.5                                                                               9.0                                                                               10.0                                                                              9.0                                                                               9.0                                                                               8.0                                                                               7.0                                    Wheat  0.0                                                                               0.0                                                                               0.0                                                                               0.0                                                                               1.0                                                                               0.0                                                                               1.0                                                                               0.0                                                                               0.0                                                                               0.0                                                                               1.0                                                                               0.0                                    Soybeans                                                                              7.0                                                                               6.5                                                                               5.5                                                                               3.0                                                                               1.5                                                                               1.0                                                                               4.0                                                                               2.5                                                                               5.0                                                                               2.0                                                                               1.5                                                                               0.5                                    Velvetleaf                                                                            8.5                                                                               8.0                                                                               8.5                                                                               4.5                                                                               7.0                                                                               2.5                                                                               10.0                                                                              l0.0                                                                              9.5                                                                               8.5                                                                               8.5                                                                               5.0                                    Dry Beans                                                                             8.0                                                                               7.0                                                                               8.0                                                                               5.0                                                                               7.5                                                                               3.5                                                                               9.0                                                                               9.0                                                                               9.0                                                                               8.0                                                                               8.0                                                                               4.0                                    Corn   4.0                                                                               4.5                                                                               4.0                                                                               2.5                                                                               1.0                                                                               1.0                                                                               2.5                                                                               3.0                                                                               2.0                                                                               4.0                                                                               0.5                                                                               1.0                                    Sunflower                                                                             9.0                                                                               l0.0                                                                              8.5                                                                               8.5                                                                               8.0                                                                               5.5                                                                               9.5                                                                               l0.0                                                                              9.0                                                                               l0.0                                                                              9.0                                                                               8.5                                    **Pigweed                                                                             9.5                                                                               8.5                                                                               9.0                                                                               7.5                                                                               7.0                                                                               5.0                                                                               9.0                                                                               9.0                                                                               9.5                                                                               8.5                                                                               9.0                                                                               8.5                                    __________________________________________________________________________      + Averaged plant response of two replications taken l7 days after              treatment.                                                                     o Averaged plant response of two replications taken 34 days after              treatment.                                                                     Rating scale 0-10,                                                             0 = no control;                                                                10 = 100% control.                                                       

TEST H

A field test site containing Matapeake silt loam soil with 10% organic matter content was plowed and disced in preparation for seeding. Just prior to final discing, 500 lbs/a of 10-10-10 fertilizer was applied to the soil. Twenty-eight crops and five weed species were drilled. Shortly after planting chemical treatments were applied to the soil surface of the plots. All treatments were replicated twice. Within five days after the application, 2.5 cm of water was applied to plots using overhead sprinkler irrigation. Evaluation of the effect of the chemicals began 30 days after application. The effect of the chemicals on crops and weeds was rated on a scale of 0-100 where 0 represented no effect and 100 represented complete kill. Untreated controls were included in the experiment for comparison. The results obtained are presented in Table H. It will be seen that certain compounds form the scope of the invention can be used for selective pre-emergence weed control in such crops as soybeans, corn, wheat, cotton, flax and lima beans.

                  TABLE H                                                          ______________________________________                                         Pre-Emergence Multicrop Field Test                                             % Effect.sup.1                                                                           Compound No.                                                                   3           9                                                        kg ai/ha    .03l   .062    .125 .062 .125 .250                                 ______________________________________                                         Safflower   0      0       0    5    65   90                                   Sunflower   0      0       0    0    45   9O                                   Corn        0      0       5    0    5     0                                   Sorghum     5      0       5    0    30   90                                   Clover      0      0       0    0    0    20                                   Alfalfa     0      0       0    0    10   30                                   Soybeans    0      0       5    0    0     0                                   Suarbeets   0      0       0    0    0    30                                   Rape        0      0       5    l5   85   100                                  Squash      0      0       0    0    0    60                                   Potatoes    0      0       5    0    l5   40                                   Cucumbers   l0     0       0    20   5    20                                   Lespedela   0      0       10   0    0    30                                   Wheat       0      0       0    0    0     0                                   Rice        45     0       l0   0    0    70                                   Okra        0      0       5    0    0    10                                   Oats        0      0       0    0    0    60                                   Cotton      0      0       0    0    0     0                                   Carrots     0      0       0    0    5    80                                   Red beets   0      0       0    5    5    20                                   Cabbage     0      0       0    0    35   90                                   Endive      0      0       10   0    0    --                                   Flax        5      0       0    0    0     0                                   Spinach     10     0       5    0    0    70                                   Snap beans  l0     0       5    0    0     0                                   Tomatoe     0      0       5    10   0    10                                   Peanuts     --     --      --   --   --   --                                   Lima beans  0      0       0    15   0     0                                   Velvetleaf  0      0       0    0    0    70                                   Wild Oats   0      0       0    0    25   10                                   Ryegrass    0      0       5    5    35   20                                   Barnyardgrass                                                                              0      0       0    0    25   60                                   Foxtail     5      5       15   10   35   70                                   Crabgrass   0      0       0    0    30   70                                   Ragweed     l0     0       5    5    35   70                                   lambsquarter                                                                               15     0       25   10   25   60                                   Smartweed   0      --      10   0    30   70                                   Purscane    --     0       0    --   --   --                                   Jimsonweed  0      --      --   0    0    60                                   Pigweed     0      0       --   0    --   60                                   Morningglory                                                                               0      0       0    0    0    50                                   Nutsedge    0      0       0    0    0    --                                   Flower-of-an Hour                                                                          15     0       10   10   10   70                                   ______________________________________                                          .sup.1 0 = no effect; l00 = complete kill.                               

TEST I

A post-emergence field test was conducted using the same plantings as described in Test H. Twenty-one days after planting, chemical treatments were applied to emerged crops and weeds in each plot. All treatments were applied in water containing 0.1% surfactant and were replicated twice. Evaluation began 30 days after application. Again, the effect of a treatment on crops and weeds was rated on a scale of 0-100, where 0=no effect and 100=complete kill. Untreated controls were included in the experiment for comparison. The data are summarized in Table I.

The compounds tested provided excellent post-emergence weed control in a number of crops, including corn, wheat, oats, potatoes, flax and tomatoes.

                  TABLE I                                                          ______________________________________                                         Post-Emergence Multicrop Field Test                                            % Effect.sup.1                                                                         Compound No.                                                                   3             9                                                        kg ai/ha  .015    .031   .062   .031 .062   .125                               ______________________________________                                         Safflower 85      90     95     90    100   100                                Sunflower 90      90     90     95   100    100                                Corn      0       20     45     0    0      0                                  Sorghum   90      90     90     95   90     95                                 Clover    25      50     65     65   75     85                                 Alfalfa   55      55     75     65   70     70                                 Soybeans  25      50     65     25   50     70                                 Sugarbeets                                                                               15      15     50     25   30     35                                 Rape      55      75     65     95   95     100                                Squash    65      70     80     85   85     95                                 Potatoes  0       5      10     0    0      15                                 Cucumbers 30      45     45     5    10     35                                 Lespedela 70      65     70     70   70     95                                 Wheat     0       0      20     0    0      0                                  Rice      25      30     30     35   40     45                                 Okra      10      60     55     55   60     65                                 Oats      0       5      10     0    0      15                                 Cotton    45      50     70     80   70     70                                 Carrots   20      40     85     90   85     95                                 Red beets 30      45     90     90   90     95                                 Cabbage   25      60     75     80   90     100                                Endive    20      --     --     --   --     --                                 Flax      0       20     15     10   25     45                                 Spinach   45      90     90     90   95     100                                Snap beans                                                                               55      65     75     55   80     85                                 Tomatoe   5       0      10     0    5      15                                 Peanuts   --      --     --     --   --     --                                 Lima beans                                                                               5       60     70     80   85     90                                 Velvetleaf                                                                               55      95     95     90   100    100                                Wild Oats 10      10     15     5    40     30                                 Ryegrass  5       5      25     20   70     60                                 Barnyardgrass                                                                            0       0      10     80   90     90                                 Foxtail   10      5      35     5    40     50                                 Crabgrass --      0      40     --   10     --                                 Ragweed   55      70     85     70   80     85                                 Lambsquarter                                                                             30      90     75     55   70     70                                 Smartweed --      --     80     60   90     80                                 Purscane  --      --     90     --   90     85                                 Jimsonweed                                                                               --      --     30     0    --     0                                  Pigweed   40      90     85     80   90     85                                 Morningglory                                                                             --      --     --     --   --     --                                 Nutsedge  --      --     --     0    --     --                                 Flower-of-                                                                               70      80     75     70   90     80                                 an Hour                                                                        ______________________________________                                          .sup.1 0 = no effect; 100 = complete kill.                               

TEST J

In a pre-emergence field test study, Matapeake silt loam soil with 1% organic matter content was plowed and disked in preparation for seeding. Just prior to final discing 500 lbs/a of 10-10-10 fertilizer was applied to the soil. Corn was planted into single row plots. Shortly after planting, chemical treatments were applied to the soil surface of the plots. All treatments were applied in water. The experiment was designed as a partially randomized complete block with 3 replications. The first replication was layed out in numerical sequence and not randomized. Evaluation of treatments began 43 days after application. The effect of a treatment on crops and indigenous weeds was rated on a scale of 0-100, where 0=no effect and 100=complete kill. Untreated controls were included in the experiment for comparison. The results obtained are given in Table J.

It will be apparent from Table J that the compound tested can be used for selective pre-emergence weed control in corn.

                  TABLE J                                                          ______________________________________                                         Pre-Emergence Corn Field Test                                                  % Effect.sup.1                                                                           Compound No.    Untreated                                                      9               Control                                              kg ai/ha    0.031  0.062   0.125                                                                               0.250 Cult.                                                                               Uncult.                             ______________________________________                                         Corn         0      3       0    7    0    0                                   Fall Panicum                                                                               53     73      80   93    --   0                                   Crabgrass   43     57      70   90    --   0                                   Yellow Foxtail                                                                             53     63      80   90    --   0                                   Purslane    70     87      86   96    --   0                                   Flower-of-an-hour                                                                          53     70      80   90    --   0                                   Galinsoga   --     --      --   --    --   0                                   Velvetleaf  33     57      90   90    --   0                                   ______________________________________                                          .sup.1 % effect: 0 = no effect; 100 = complete kill. Average of 3              replications.                                                            

TEST K

For a post-emergence field test, a site as described in Test J was selected. Twenty-one days after planting the corn chemical treatments were applied to the emerged crop and weeds in each plot. Each treatment included applications to both previously untreated plots and to plots which earlier had received a pre-emergence application of alachlor herbicide. All treatments were applied in water. The experiment was designed as a partially randomized complete block wtih 3 replications. The first replication was layed out in numerical sequence and not randomized. Evaluation of treatments began 39 days after application. The effect of a chemical on corn and indigenous weeds was rated on a scale of 0-100, where 0 is no effect and 10 is complete kill. Untreated controls were included in the experiment for comparison. The data, shown in Table K, indicate the potential utility of a compound from the scope of the present invention for selective post-emergence weed control in corn, both when applied by itself or in conjunction with a prior pre-emergence treatment of alachlor.

                  TABLE K                                                          ______________________________________                                         Post-emergence Corn Field Test                                                 % Effect                                                                              Compound No. 9                                                          kg ai/ha 0.031   0.062  0.125  0.250                                                                               Cult   Uncult                              ______________________________________                                         w/o Alachlor                                                                   Corn     0       7      0      30   0      3                                   Fall Panicum                                                                            0       7      20     27   --     0                                   Purslane 37      60     53     70   --     0                                   Galinsoga                                                                               --      --     --     --   --     0                                   Flower-of-                                                                              --      --     --     80   --     0                                   an-Hour                                                                        with Alachlor                                                                  Corn     0       3      0      23   0      0                                   Fall Panicum                                                                            100     100    100    97   --     100                                 Purslane 100     100    100    100  --     97                                  Galinsoga                                                                               100     100    --     100  --     100                                 Flower-of-                                                                              95      100    --     100  --     87                                  an-Hour                                                                        ______________________________________                                          .sup.1 % Effect, 0 = no effect, 100 = complete kill.                     

TEST L

This field test was conducted on a site as previously described for tests H through K. Wheat, wild oats and mustard were drilled into plots. Herbicide treatments were applied in the spring when wheat was fully tillered and 12-20 cm tall. All treatments were applied in water. The experiment was designed as a partially randomized complete block with 3 replications. The first replication was layed out in numerical sequence and not randomized. Evaluation of treatments began 25 days after application. The effect of a treatment on crops and weeds was rated on a scale of 0-100, where 0=no effect and 100=complete kill. Untreated controls were included in the experiment for comparison. The data, presented in Table L, indicate that the test compound provides control of certain weed species without injuring the crop when applied post-emergence to wheat.

                  TABLE L                                                          ______________________________________                                         Post-Emergence Spring Wheat Field Test                                         % Effect.sup.1                                                                           Compound No.                                                                   3                Untreated                                           kg ai/ha    .008   .015    .031  .062  Control                                 ______________________________________                                         Wheat       0      0       0     0     0                                       Yellow Foxtail                                                                             0      3       7     7     0                                       Ragweed     0      7       17    27    0                                       Wild Oats   0      0       0     0     0                                       Velvetleaf  3      7       3     3     0                                       Flower-of-an-hour                                                                          3      10      3     3     0                                       Mustard     40     65      --    --    0                                       Wheat Yield.sup.2                                                                          169    223     190   259   203                                     ______________________________________                                          .sup.1 % Effect  0 = no effect, 100 = complete kill; Average of 3              replicates.                                                                    .sup.2 Wheat Yield  Yield from all 4 rows/plot. Data Average of 3              replicates.                                                              

TEST M

For a pre-plant incorporated field test on winter wheat, a Keyport silt loam with 1% organic matter content was plowed and disked in preparation for fall seeding. Just prior to final disking 500 lbs/a of 10-10-10 fertilizer was applied to the field. Chemical treatments were then applied to the soil surface of plots. All chemicals were applied in water. Immediately after application the chemical was incorporated into the upper 5 cm of soil utilizing a rototiller. Wheat, wild oats and wild mustard were then drilled into plots. The experiment was designed as a partially randomized complete block with 3 replications. The first replication was layed out in numerical sequence and not randomized. Evaluation of the treatments was made 31 days after application. The effect of a chemical on wheat and weeds was rated on a scale of 0-100, where 0=no effect and 100=complete kill. Untreated controls were included in the experiment for comparison. The test results are tabulated in Table L. The test chemicals used as pre-plant incorporated treatments provided excellent control of mustard without causing injury to the wheat crop.

                  TABLE M                                                          ______________________________________                                         Pre-plant incorporate field test on wheat                                      % Effect.sup.1                                                                 (31 days after treatment)                                                      Compound                      Wild Wild                                        No.        Kg ai/ha Wheat     Oats Mustard                                     ______________________________________                                         3          .062     0         0    60                                                     .125     0         0    90                                                     .250     0         3    90                                          9          .062     0         0    90                                                     .125     0         0    90                                                     .250     3         3    90                                          Untreated  --       0         0    0                                           Control                                                                        ______________________________________                                          .sup.1 Effect  0 = no effect, 100 = complete kill.                       

TEST N

For a pre-emergence field test on winter wheat, a site as described in Test M was selected. Wheat, wild oats and wild mustard were drilled into the plots and herbicide treatments were applied to the soil surface of the plots immediately after planting. All treatments were applied in water. The experiment was designed as a partially randomized complete block with 3 replications. The first replication was layed out in numerical sequence and not randomized. Evaluation of treatments were made 31 days after application. The effect of a chemical on wheat and weeds was rated on a scale of 0-100, where 0 =no effect and 10=complete kill. Untreated controls were included in the experiment for comparison. The ratings are presented in Table N.

The chemicals used in this test provide excellent pre-emergence weed control in wheat.

                  TABLE N                                                          ______________________________________                                         Pre-emergence Field Test on Wheat                                              % Effect.sup.1                                                                 (31 days after treatment)                                                      Compound                      Wild Wild                                        No.        kg ai/ha Wheat     Oats Mustard                                     ______________________________________                                         3          .062     0         0    83                                                     .125     0         0    90                                                     .250     0         0    90                                          9          .062     3         0    90                                                     .125     0         0    90                                                     .250     3         10   90                                          Untreated  --       0         0     0                                          Control                                                                        ______________________________________                                          .sup.1 % Effect  0 = no effect, 100 = complete kill.                      

What is claimed is:
 1. The compound of claim 1 which is N-[(4-methoxy-6-methylpyrimidin-2-yl)-aminocarbonyl]-2-(propylsulfinyl)benzenesulfonamide.
 2. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid diluent.
 3. A method for controlling growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the compound of claim
 1. 